Dessert Course

By Shannon Christophe

Published on Jul 20, 2019

Transgender

Coffee and Cream

by Shannon

Tom knocked on the Loftins' front door.

"Come on in!" George called out. "You have a key, you know," he reminded the younger man as he walked into the den.

"I know. But I didn't recognize the car in the driveway, so I didn't want to presume."

"Ah. New neighbor," George explained. "Ms. Crowder. Bought the little green house two streets over."

"Drat!" Tom said. "I wanted that one."

George laughed. "It wasn't going to stay empty that long. You have to be at least 65 before you can join the community, you know. Keeps our yards free of hooligans like you and your woman." He shook his empty glass in mock anger at Tom. "Where is she, by the way?"

"She had a work emergency. Some kid pitched a tantrum and threw his drink on a Regency portrait."

"Pity. Tell her she was missed."

"Will do. Speaking of better halves..."

George hooked a thumb back towards the bedroom. "Counseling session. Ms. Crowder is a recent widow. She comes to Anne for advice."

"That's nice of Anne," Tom said. "Need a refill?"

"Please and thanks."

The two men chatted about this and that. Eventually, the bedroom door opened and Anne walked into the den, followed by an older black woman. Tom stood up to greet them.

"Oh hi, Tom," Anne said, kissing his cheek. "I didn't hear you come in. Kelly?"

"Working late."

"Shame. Tom? Meet our newest resident, Ms. Evangeline Crowder. Lily? Tom Clarke, a dear friend and amazing pastry chef. You'll get to sample his creations at the party in a few weeks."

"If they'll have me back. Pleased to meet you, Ms. Crowder." He shook her hand. Evangeline was a slender woman with thick, wavy hair dropping past her shoulders, and showing not a bit of gray. Warm brown eyes shined up at Tom. Her eyeshadow was a light blue, and her sharp cheekbones bore a light pink blush. The same pale pink colored her full lips. She was dressed in a very nice blue blouse and matching skirt, cut to fit generous curves. Black hose disappeared into casual blue pumps.

"And you as well, young man. Goodness! Aren't you a handsome fellow?" She smiled.

"Thank you, ma'am," Tom replied.

"And so polite! Your mama did good, son."

Tom glanced briefly at Anne at the word "mama" and smiled back at Ms. Crowder. She bade everyone goodbye, saying that she hoped to see them again soon.

"I'll walk you out, Lily," Anne said, and escorted the woman to the door. They kissed cheeks and parted.

"So how was the counseling session?" George asked as his wife returned to the den.

"A bit intense, but very good overall, thank you," Anne replied, going into the kitchen for a glass of water.

"I'm sure it was," Tom said. "Intense, I mean."

"Why?" Anne asked.

"She missed a buttonhole on her blouse. Had to have been talking hard to overlook that."

"I think I sprained my tongue," Anne said, gently pinching the tip between her thumb and index finger.

"Talking can do that," George said.

"Hush, you," Anne replied, taking a seat on the couch and curling her shapely legs under her. "Start the movie. Boy toy, feed me popcorn."

"Yes, Mama," Tom grinned.


A week later, Tom was at the grocery store when he noticed a familiar face.

"Ms. Crowder!" he said. "Hello, again."

"Mr. Clarke. Good to see you."

"Please, call me Tom."

"Okay, Tom. I'm Lily to my friends."

"May I call you Lily?"

"Of course! Any friend of Anne and George..." She smiled and looked at his cart. "Doing a little bit of baking?"

Tom laughed. He had a dozen ten-pound bags of flour in the cart, half as many of sugar, plus a few tubs of butter and several egg cartons. "I usually get all this in bulk from the restaurant supply store, but their delivery driver was running late, and I have a corporate party to cater tomorrow. I couldn't chance waiting."

"I was going to ask for your secret to staying thin if that was your usual shopping list."

"You have nothing to worry about on that score, Lily."

She slapped his arm. "Flatterer! What are you making, anyway?"

"Cupcakes," Tom said wearily. "Lots and lots of cupcakes. More cupcakes than I ever want to see in one place ever again."

"Oh! Those are my favorite," Lily admitted.

"Will you be visiting Anne and George again anytime soon? I always drop off a box of extras. I'm sure they'd be happy to share."

"I see why they keep you around," Lily said with a laugh.

"I try to help out the decrepit old folks if I can," Tom said. "It's good karma."

"Hey!" Lily protested "I'm a decrepit old folk! Mind your elders!"

"Elder, maybe, but certainly not decrepit," Tom replied with a wink.

"Hmmmph," she said in disbelief, but she had a pleased smile on her face. "To answer your question, no; I haven't made any plans to visit them."

"Oh. Well, I'd be happy to drop off a box for you, too. You're right out that way."

"It's a kind offer, but I don't want to inconvenience you."

"Absolutely no trouble. It'd be my pleasure."

"Then I'm pleased to accept," she said with another smile.

"Favorite frosting?"

"Plain old vanilla."

"Done," Tom nodded. I'll be by around four tomorrow, if that's convenient."

"It is. Thank you again, Tom."

"Good to see you, Lily."

The next day, Tom pulled his car into Ms. Crowder's driveway. He and Kelly got out and walked onto the porch. Tom rang the bell.

"Coming!"

Lily opened the door and gave Tom a brief hug. "And who is this lovely young woman?" she asked, looking at Kelly.

"Lily? Meet Kelly. She's tagging along with me today. Kelly? Ms. Evangeline Crowder."

"Lily, please. Are you Tom's wife?"

Kelly smiled. "Girlfriend, though it sounds odd for a 44-year-old woman to say that. These are for you." She handed over a pastry box.

Lily opened the lid and smiled. "These look delicious! And sprinkles!" She laughed. "Thank you, Tom. I hope you won't be offended if I don't eat all six."

"Not at all. I packed extras in case this one snuck into the box." He pointed his thumb at Kelly.

"Hey!" she protested. "I can control myself, you know. Especially when they're someone else's."

"You steal my desserts all the time," Tom pointed out.

"Sure. But those are yours. Duh." She rolled her eyes conspiratorially at Lily. "Men," she groused.

Lily laughed and patted Kelly's hand. "You're welcome to get in my box any time, dear."

"Thank you, Lily. Well come on, man. Don't want to be late."

"George and Anne send their best. Enjoy those!" Tom called back on his way to the car.

"I will!" Lily replied. She waved and shut the door.

The younger couple got in the car and put their seatbelts on.

"She did not mean that the way I took it," Kelly said with a grin.

"Who knows?" Tom said as he started the car and backed out of the drive. "Ask Anne about her `counseling sessions' sometime."


"She's lonely, the poor dear." Anne was chatting with Kelly over brunch. "Her husband died only last year, but he'd had Alzheimer's a long time, so she's really been alone that much longer."

"Oh that's awful," Kelly said.

"Makes me doubly grateful that George is so healthy," Anne agreed. Then she laughed. "I think Lily is grateful, too," she confided.

"So you three...?" Kelly asked.

The older woman nodded. "Oh yes. Lily is definitely part of the harem now."

Kelly laughed. "What was her reaction to George in his frills?"

Anne chuckled. "She loved it. Apparently, her husband Harold was just as adventurous back in the day."

"Lucky girl."

Anne smiled around her glass. "Aren't we all?"


"Special delivery!" Tom called out as he walked into the den. He placed a fresh apple pie on the table.

"You're not a buxom redhead," George noted from the couch.

"No; I just passed her in the kitchen," Tom said, pointing behind him. "Why? Did you need another one?"

"Dear god, no," the older man said. "One's enough trouble."

"I heard that!" Anne called from the kitchen. "I hope you enjoyed the last time we had sex, because it was!"

"I've still got Tom to keep me warm on those long cold nights, so nyahhhh."

"Not tonight, you don't," Anne replied, appearing around the corner. She was drying her hands on a dishtowel. "Lily asked me if she could borrow our young couple for the evening. Something about `helping decrepit old folks'?" She raised an eyebrow at Tom, who laughed.

"Have we been insulted?" George asked. "I think we've been insulted."

"Look!" Tom exclaimed, pointing to the pie. "Extra cinnamon in the crust!"

"What insult?" George said, gesturing for a slice. Tom wiped his brow with a "Whew! Close one," and passed a plate over to the older man, who dug in cheerfully.

"So what are we doing tonight?" Tom asked Anne.

"Well there's always something around a house that needs fixing," the older woman replied, "But if I had to guess, I'd say you two will be doing Lily." She patted Tom's cheek. "Shave."


Lily opened the door to Tom's knock. "Welcome!" she said, inviting the younger couple in. They followed her into a small den. A couch faced the fireplace with a matching chair to one side, forming a small conversational group. Bookcases took up most of the rest of the space, with the odd small table here and there. Pictures of Lily and Harold covered the walls, and travel mementoes were scattered throughout.

Lily directed Tom and Kelly to the couch, while she took the chair. "Don't you two look nice?" she observed. Tom had on a black suit with a red shirt and no tie. Kelly was wearing a pale yellow dress and matching pumps.

"Thank you, Lily," Kelly said. "You're no slouch, either." The older woman wore a white silk blouse, black pencil skirt, black stockings, and black high heels. The blouse looked fantastic against her dark skin, and she'd accessorized with tasteful gold earrings and a thin gold necklace.

"Can I get you anything? Coffee?"

"Only if it's no inconvenience," Tom said.

"Not at all," Lily said, rising from her chair.

"I'll help you," Kelly said, standing up.

"Thank you, dear," Lily said, and the two women disappeared into the kitchen.

When they returned, Kelly sat in the chair, while Lily took a seat next to Tom.

"Um... did you forget the coffee?" Tom asked.

Kelly chuckled. "There was never going to be coffee, Tom. That was just an excuse for me and Lily to have some private girl talk in the kitchen."

"Wow," he said. "I totally didn't pick up on that."

Kelly pointed at him. "Boy."

Lily patted Tom's knee. "I explained to your young woman that I wanted to be selfish tonight. Anne is very talented with her magic wand, and George is a dear, but it's been twenty years since I had a young, hard cock inside me, and I didn't want to be distracted. She graciously consented."

Tom looked at Kelly, who grinned. "Don't mind me. I'll be over here keeping score."

Tom laughed and turned back to Lily. "Seems I'm all yours, then," he smiled.

The two leaned forward for their first kiss. Lily was wearing dark red lipstick on her full lips, and Tom could feel it sticking slightly to his mouth. Their tongues wrapped around each other, exploring. Tom held on to Lily's waist as she put her arms around his shoulders, pulling him in tighter.

When they broke apart, Lily sighed. "You're a very good kisser," she said to Tom.

"He has a talented tongue, for sure," Kelly said.

"Oh I hope so," the older woman replied, pulling Tom in for another deep kiss. This time, their hands roamed around. Lily rubbed Tom's arms and legs and back, squeezing his thighs and biceps. Tom traced the curves from Lily's neck to her shoulders and down her arms, returning to rub up and down her ribs and slide along the swells of her large breasts. The white silk of her blouse felt great under his palms as he moved from the sides of Lily's breasts to the front, gently squeezing and lifting.

Lily hummed with pleasure as Tom's thumbs brushed over her nipples, and she started working on the buttons of his shirt. She pulled it off of him, exposing his deep blue lace bra. Lily dipped a hand inside the cup, her long red nails flicking over Tom's nipple, making it stand to attention. She kept kissing him as his hands went to her blouse buttons.

Tom pulled the blouse aside, revealing Lily's smooth, shiny black bra. He'd always found black women in black lingerie incredibly arousing, and he bent down to trail kisses across the tops of her huge tits and into the deep cleavage. One hand slipped under her skirt, running along her leg. He felt the lacy tops of her thigh high stockings, then the smooth nylon of the older woman's panties. He lightly rubbed across the front, moving between her inner thighs, and she sighed and spread her knees further apart. His thumb teased her clit and she started breathing faster. Tom kept rubbing as he pulled Lily into another deep kiss, and she suddenly clutched his arm tight, moaning into his mouth as her first orgasm rolled through her.

"Oh wow," she said when she'd caught her breath. "And that was with our clothes on. I can't wait to get you naked."

"Same here," Tom agreed, standing up and pulling the older woman up to stand in front of him. He slipped her blouse off, then knelt to slide the skirt down her legs. He kissed Lily's pussy through her black panties, inhaling the musk of her, then slid them down as well, revealing a bald cunt. Lily shaved completely. He dipped his tongue in between her bare pussy lips for a few moments, keeping her clit hard, then stood back up. He reached around her back, undoing the hooks of her bra. The nylon straps slid down her arms, and she tossed the bra onto the pile of clothes behind her. Her breasts were bigger than Kelly's, but not quite as large as Anne's. They sagged a little bit, but kept their shape even so. Her dark areolas were the size of silver dollars, and her black nipples were thick and erect. She stood before Tom in just her stockings and heels.

"Beautiful," he said, and behind him, Kelly agreed.

"Thank you," Lily said. She reached for Tom's belt and zipper and pushed his pants down. His hard-on bulged in thin blue panties, and his cock jutted out of the waistband, the tip just brushing the bottom of his white garter belt. Lily nuzzled his cock happily.

"You feel amazing," she said. "Let me get these panties out of the way so I can get a proper taste." She slipped the thin material down his legs, and her hands rubbed his white stockings on the way back up. Tom reached behind him. "No," Lily said. "Leave the bra; it's sexy." She winked at him and took his cock into her mouth, licking and sucking along the hard shaft. Tom held her head, watching the dark red lips envelop him. The contrast between his skin and hers was driving him wild!

As Lily continued sucking him, Tom bent down to take her heavy tits in his hands. He rolled her thick nipples in his fingers, lightly pulling and pinching them. She hummed in pleasure, the vibrations of it traveling straight down Tom's cock, making him even harder. He felt his balls start to swell, and gently stopped Lily.

"Your turn," he said.

She smiled and sat back on the couch, scooting her hips to the front, then leaned back and opened her legs wide. Her hands slid down to spread her pussy open for Tom. The bright pink was shocking against her chocolate skin, and he dove into it face first. Lily gasped and moaned as Tom expertly ate her out, sucking the labia into his mouth, licking the clit, and plunging his tongue deep inside the older black woman's cunt. He teased her brown asshole with one finger as he went down on her, and she panted "yes!" He tongued her asshole thoroughly to get it slick, then slowly pushed his finger in.

Lily rode the waves of Tom's attention, clenching her ass around his finger and pulling his head deeper into her pussy until she cried out in fulfillment, clutching his arms as she shuddered and shook.

"Damn, you guys are hot," Kelly said from the chair. Tom looked over to see that the brunette had ditched her clothes entirely. She had a leg propped on the arm of the chair, and one hand was two fingers deep inside her cunt as the other squeezed her tit and played with her nipple.

Tom grinned at her and tuned back to Lily. She dug her heels into his ass cheeks, pulling him closer for another deep kiss. "That was wonderful," she said. "I could let you do that all night, but you really need to fuck me now. Move so I can turn over."

Tom scooted back and Lily rolled over, spreading her knees apart and bracing herself against the back of the couch. Tom stepped closer, his cock nudging in between Lily's generous round ass cheeks, and he leaned over to grab the black woman's big tits and play with her nipples.

Lily shifted her hips back and forth, rubbing against Tom's cock. She enjoyed the attention to her tits for a bit, then reached back and spread her cheeks apart. "Fuck my pussy, Tom! Give me that hard cock!"

Tom sank deep into Lily's wet cunt. His balls slapped against the older woman's thighs as he rocked in and out of her, and her pendulous tits swayed in time, making Kelly masturbate even faster at the sight. Tom placed his hand at the top of Lily's ass. He tickled her asshole for a moment, then slowly pushed his thumb inside her. He could feel his cock on the other side as it pumped back and forth.

"Oh yes!" Lily cried. "Fill me up! Oh yes! Oh yes! OH YES!" She orgasmed hard, and Tom felt his cock swimming in her cunt juices. That pushed him over the edge, and he added his own hot cum to the flood. Kelly cried out as she, too, came in a rush.

The three panted as they cooled down, no one moving very much or very fast. Tom looked over at Kelly.

"How'd we do, coach?"

The brunette grinned at him. "9.3. It would have been higher, but the Russian judge only gave you a six."

"Sneaky communists."

Lily laughed. "You two are funny."

"If you can't laugh during sex," Kelly said, "you're with the wrong person."

"Amen to that," the older woman replied. Tom helped her up, and she stepped into the hall, returning with towels for everybody. They all did a quick clean and got dressed again.

"Now," Lily said, giving Tom another thorough kiss, "coffee for real!" Kelly laughed and went to help.

Enjoy older crossdressers? Me, too! Feedback is always welcome. Send comments, suggestions, or just say hi! shannon.christophe@yahoo.com

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Next: Chapter 7


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