The Coffee Shop - Cover

The Coffee Shop

Copyright© 2019 by Unca D

Chapter 2

Romantic Sex Story: Chapter 2 - 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  

Sierra brought a pair of rocks glasses from her kitchen with some ice in each, then opened a bottle and poured some in each. She handed one to him and sat beside him on the sofa.

Glenn regarded the amber liquid in his glass. “What Bourbon is this?”

“Taste it.”

He sipped it. “Mmm ... Very nice. Lighter than your usual.”

She sipped from her glass. “It’s a baby Bourbon from here in this state.”

“I thought Bourbon had to come from Kentucky.”

“Kentucky Bourbon has to. So long as it’s fifty-one percent corn mash and they don’t call it Kentucky, it’s legally Bourbon.”

“This is very nice ... and it’s a nice place you have here, Sierra. I like older buildings. The place has charm.”

“It’s got charm and then some,” she replied. “As you said, nothing beats living over the store.”

Glenn took another sip and held it in his mouth to savor the flavor and aroma. He felt something against the back of his calf, looked down and saw it was Sierra’s toe. He looked in her eyes and she smiled.

“Assuming I’m not misinterpreting,” he said, “I’m not accustomed to getting this sort of an invitation on a first date.”

“I don’t extend this sort of an invitation on a first date. This doesn’t feel like a first date to me, Glenn. You’ve been a regular in my shop practically from the day we opened. You’ve always treated me and my staff well, tipped generously ... have been patient with us when we’re busy or when we screw up. I feel like I know you. The topper was yesterday when you brought me the payoff from that race. You didn’t have to do that.”

“Yes, I did. It was money you won, fair and square.”

“You could’ve told me anything. You could’ve told me my horse lost and then kept it all and I’d be none the wiser. This is how I know I can trust you, Glenn. I’ll tell you -- that hundred will come in handy. I have an insurance bill I forgot about that’s due this week, but the rent checks aren’t due until the week after. I was about a hundred short and didn’t know where the funds were coming from. Those winnings will pretty much cover it.”

Glenn patted his lap and Sierra shifted to sit on it. He put his arm around her and caressed her cheek. Then he lifted her black-rimmed glasses from her face. “It’s not a strong prescription you wear. Do you need these?”

“They’re to correct rather bad astigmatism in my right eye,” she replied.

Glenn set them on the end table. He looked into her gray eyes. “You don’t wear eye makeup,” he remarked.

“I don’t wear any makeup. Why bother? I know I’m not much to look at.”

“That’s not true. I think you’re very attractive. You have a pretty face.”

“I have a nerdy face,” she replied, “especially with my glasses on. So, if you like nerdy girls...”

“I love nerdy girls.” He kissed her lips.

“Mmm ... I liked that.” She pressed her hand against her chest. “My heart is slowing down. It was going pretty fast a few moments ago.”

“Afraid I’d turn you down?” he asked.

“Yeah ... plus I was afraid you’d accept. You’re putting me at ease, Glenn.” He kissed her again. “I don’t have an opportunity to get out much, with the shop and Jack ... although he’s getting old enough to be a latchkey kid.”

“You must meet all sorts of interesting guys in your shop.”

“It’s my policy not to date customers. I’m making an exception in your case.”

“We do have a problem,” he said. “I don’t have any condoms with me. I generally don’t carry them. If it’s not too much of a passion-killer I could go out...”

“It’s all right -- I have some. I bought some this morning.”

“So, you had this all planned?”

“I like to be prepared,” she replied. “I didn’t know what would happen today, but today couldn’t have gone better. Your concern for my protection is another way I know I can trust you. And, how accepting you are of Jack -- that’s the cherry on the sundae.”

Glenn ran his hand along her shin and knee. “You have pretty legs, Sierra ... long and sleek” He explored the muscles in her calf.

“I’m happy with them.”

He stroked her left forearm. “That’s quite a tattoo,” he said as he ran his finger over the large and elaborate rose inked into her skin.

“I had that done to hide some gang signs,” she replied.

He looked into her eyes. “You’re kidding.”

She smiled and giggled. “Yes, I’m kidding. I got that on my eighteenth birthday while I was still pregnant with Jack. I got it because I could.”

“Do you have others?” he asked.

“Maybe that’s for you to find out.”

Glenn caressed her back and found the zipper that closed her dress. He unzipped it all the way down, eased her arms from the arm-holes and lowered the bodice. Underneath she wore a black bra with lace trim. He traced the outline of the shoulder straps, down across the tops of the cups and up again.

Slipping his finger under the fabric he drew it across her areola and nipple and he saw tension drain from Sierra’s face. Her eyelids drooped and her lips parted. Glenn repeated his stroke. “That feels really good, Glenn,” she said. “It’s been a long time.”

“Is there a chance that Jackson will wander through here?”

“You’re right,” she said as she slipped her arms back into her dress and pulled it up. “We should adjourn our business here and reconvene in my bedroom.”

Holding hands they headed for her bed-chamber. Sierra opened a drawer in her nightstand and removed the box of condoms. After tearing off the cellophane wrapper she opened it and removed a strip of them. “I’ll leave these here where they’re handy,” she said as she set the strip on her nightstand and returned the box to its drawer. She set her alarm clock. “I need to get up at five so I can go down and get the shop ready to open. I’m sorry about that.”

“I understand. You open at six.”

“Wilma will be here by six and when she comes in I can come back up here and take my shower and get Jack’s breakfast ready. I think it’s best if you’re on your way before Jack gets up -- at least for tonight.”

“Understood. Are you looking for something long-term in a relationship?”

“I am,” she replied, “but I’m also a realist. It’s been a long time since I’ve felt this way about a guy ... and I like how it feels.”

“It’s been a long time for me, too,” he said. “In fact, not since Darlene passed.”

“Darlene was...”

“My late wife.”

She caressed his cheek. “I am so sorry you lost her that way.”

“I think after five years it’s okay to move on.”

Glenn helped her lift her dress over her head and set it on a chair. He slipped out of his shorts and polo shirt and then regarded her wearing only her bra and matching briefs. “You have a nice body,” he remarked.

“I was going to say the same about you.” They embraced, held each other tight and kissed. Glenn relaxed his jaw and admitted Sierra’s tongue into his mouth.

He sat on her bed and held her on his lap. They kissed more. “I could fall in love with you,” he said. “You are exactly the sort of woman I admire.”

“I’m glad to hear that,” she replied, “because I am already falling in love with you.”

Glenn resumed probing Sierra’s breasts under the fabric of her bra. He eased the shoulder straps down her arms and lowered the cups to expose her firm compact breasts. They were A-cup sized and adorned with wide, round, pebbly areolas surrounding thick pink nipples. “Lovely,” he said. “Those are sensational breasts with sexy nipples.”

“My nipples got so big and dark while I was pregnant,” she replied. “My doctor said they’d go back to normal but they never did. The pigment faded a bit, though.”

“I love their pigmentation -- a shade darker and a shade pinker than your complexion.” He stroked her nipples with the back of his finger. Then he teased her right breast with his tongue and drew her nipple into his mouth.

Sierra held his head, pressing his face against her breast. “That feels so good, Glenn,” she whispered.

He switched sides and mouthed her left breast. “I can feel your heart,” he said.

“There’s not much insulation between it and your lips,” she replied.

Sierra stood and took Glenn’s hand. He stood and together they turned down the covers on her full-sized bed. She lay on her back and he knelt near her and caressed her slender legs. “You have pretty knees,” he said as he smoothed his palms along her thighs.

Glenn caressed her flat abdomen, playing with her little round navel. He traced the Gothic arch of her rib cage and moved up to fondle her breasts, caressing them from back to front. “Mmm...” she purred, “a little firmer and deeper.” He squeezed her breasts with a firmer hand. “Like that -- like you’re milking them...”

Sierra’s breathing grew slow and deep. She put her hands on his and squeezed his fingers into her flesh. “Like this -- they’re not made of glass.” Following her direction he squeezed her breasts, ending the stroke with firm pinches on her nipples.

Her legs began to twitch and jerk as he fondled her breasts. He drew her right nipple into his mouth, massaging it with his tongue and

savoring the texture of her areola with its pebbly constellation of tiny glands. “Those nipples sure do get hard,” he remarked. “Getting ready for some action down south?” he asked as he cupped his hand over her mons and gave her labia a circular massage.

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