Dessert Course

By Shannon Christophe

Published on Jul 1, 2019

Transgender

But I Know What I Like by Shannon

“Knock knock!” Tom called out as he entered the kitchen. He’d visited so much in the past few weeks, the place felt like a second home, but he still announced himself whenever he dropped by.

“We’re in the bedroom!” George replied.

Tom made his way down the short hall and stopped at the doorway to the master bedroom, looking in at the older couple.

“I’m shocked,” he said. “Shocked to find fucking going on in here.”

“Thank you, Captain Renault,” George said. “Were you going to join in, or did you just stop by to quote movies at us?” His wife, Anne, chuckled from where she straddled her husband’s cock. For once, the two were completely naked, rather than wearing their usual matching lingerie.

“Actually, I have to duck right back out. We’re doing that museum thing tonight.”

“Oh, is that tonight?” Anne pouted. “We miss you.”

Tom looked at his watch and walked to the foot of the big California King bed. “I can spare ten minutes. Hop off, Mama.”

Anne raised herself up off of George’s cock and rolled over to her side of the bed. Her big droopy tits swayed hypnotically with the motion. She settled in next to her husband and parted her legs, motioning to Tom, who waved his finger back and forth between them.

“Eeny, meeny, miney…” he grinned.

“You’re a teasing bitch. You know that, don’t you, son?” George said.

“Shut up and get blown, old man,” Tom replied, wrapping his lips around George’s hard-on. He loved tasting Anne’s pussy juices on the older man’s cock.

“Fine,” Anne said. “Who needs ya?” She pulled a vibrator out of her nightstand and slipped it into her cunt, stretching with pleasure as she watched Tom suck her husband off. Tom reached over and stroked her heavy breasts, enjoying the weight of them against his hand. He pinched her thick pink nipples the way she liked.

In a few minutes, George grabbed Tom’s head and arched his hips, spilling a load into the younger man’s mouth with a moan. Tom leaned over to meet Anne heading his way, and gave her a deep kiss, sharing the hot cum. He licked a spot where some had leaked out and swallowed. “Jeez, George,” he said, slapping the man’s hip playfully. “You been saving that up?”

“Forecast called for a rainy day, so…” George replied.

“Remind me to rig a sprinkler on the house when I come back,” Tom said, standing and straightening his clothes. “See you tomorrow night, yes?”

“Yes,” Anne said. “Wear white.”

“Good times,” Tom said. “See you then!”


“There you are, Mr. Clarke.”

Tom looked up from arranging the dessert buffet to see one of the museum’s restoration experts standing at the other side of the table. “Miss Dunleavey. How are you this evening?”

“Please, call me Kelly.”

“Only if you call me Tom.”

“Deal. I wanted to review the entrees with you. We’ve had some last-minute attendee changes. The board of dir…”

Tom’s eyes wandered covertly over the woman as she spoke. She was a tall, slender brunette—what his mom would have called “willowy”—with dark brown eyes and high cheekbones. A pert nose rode over lips painted a medium red, contrasting perfectly with both her tanned skin and the blue of the dress. She was probably Tom’s age, 45, maybe a couple of years younger. Her evening gown was midnight blue, with a reproduction 17th century French brooch holding gathered fabric at one shoulder. Or hell, Tom thought, it might be the real thing, given where she works. Her other shoulder was bare. Understated thin gold bracelets and button earrings complimented the brooch. The dress had a gathered waist, outlining good hips and, from what Tom remembered from other visits, a heart-shaped ass. He wondered what she was wearing underneath. A strapless bra, for sure. She was just large enough in the bust to need the support. The panties, though. A thong? Boy shorts? I’d put her in a bikini style or briefs, he thought.

“…so I thought we could sell the kids into slavery and roast the parents over open coals,” she said.

Tom shook his head. “Wait, what?”

She laughed. “Caught you! You were undressing me with your eyes.” She waggled a finger at him in mock admonition.

“Actually,” he admitted, “I was kind of doing the opposite.”

She stood up straighter. “I think I’ve just been insulted.”

“No! That’s not what I meant. You have a great shape, and I was sort of mentally paging through a lingerie catalog to…uh…well…um…” He stammered to a stop.

She raised an eyebrow and shot a wry grin at him. “How’s that foot taste?”

“Needs more cinnamon.”

She laughed, thank goodness, then leaned closer. “Tell you what, Mr. would-be Saint Laurent; give me your best guess. If you’re right, you’ll get a surprise.”

“Well, strapless bra,” he began.

“Duh. That’s a given.” She pointed to her bare shoulder.

“And…” flip of the coin, “bikini cut.”

She pulled her mouth down, impressed. “Not bad for a boy. For the bonus round, what color?”

“Gray,” he said immediately.

“Not black?”

“That would work with the dress but not your skin tone. Gray goes with both.”

“Are you gay?”

“Not exclusively.”

“Are you married?”

“No.”

“Seeing someone?”

“A couple.”

“A couple of people or a ‘couple’ couple?”

“The latter.”

She cocked her head and looked at him. “Interesting. See me after for your surprise.” They made the final adjustments to the menu and went on with their duties.


The fund-raiser was a big success for the museum and apart from one dropped tray, for Tom’s catering company as well. He helped load the van and sent his crew home, then returned to the hall for a final look through. Kelly was chatting up an older couple, explaining some of the techniques she used to restore artwork. As the couple bent forward to look at a painting more closely, Tom was surprised to see Kelly admiring the woman’s ass. He caught her eye and raised an eyebrow. She shrugged her bare shoulder and grinned, then escorted the couple out with kind thanks and locked the doors behind them.

“Lech,” Tom said.

Kelly laughed. “As much money as they donate, I’d go to bed with either one of them. But I’d do her for free.”

“Are you gay?”

“ ‘Not exclusively’.”

“That sounds familiar.” They laughed.

She took his hand. “Come on.”

“Where are we going?”

“Your surprise, remember?” She led him through the museum until they reached the Modern Art hall. Kelly steered Tom to one of the displays, a piece of furniture that was a mash-up of a chaise lounge, settee, and couch, all joined at weird angles. It was covered in a truly hideous paisley fabric in 70s colors.

“What. The fuck. Is that?” Tom asked.

“Isn’t it awful?” Kelly replied. “It’s supposed to be a statement about changing family values or something. The artist is a horrific cunt and I hate her, so I want you to fuck me on it. Oh yeah, surprise!”

He looked at the so-called art. “I’m not sure that I can.”

“Close your eyes and think of what’s-their-names. Your couple.”

“The Loftins?”

“You have more than one couple? A couple of couples, perhaps?”

He laughed. “Just the one, and they’re enough for anyone.”

“Are you exclusive?”

“Not at all. It’s just…” He gestured at the whatever the hell it was. “…that.”

“Trust me,” she said, reaching up to undo his tie, “you’ll be fine.”

She pulled the bow tie apart and went to work on his shirt buttons as Tom drew her close for a deep kiss. His hands roamed over her hips and up her ribs, brushing the outside of her firm breasts. She hummed into his mouth. She got his shirt open and rubbed his chest, then suddenly broke off the kiss.

“No lingerie?”

“Huh?”

“Oh please. Deny it.”

“Can’t. Won’t.” He grinned.

She pouted. “I’m actually a little disappointed.”

“As erotic as it is to wear it under my work clothes, I keep having this nightmare where I spill hot soup on myself and have to rip it all off in the middle of someone’s wedding reception.”

She laughed. “Yes. I can see where that would be a problem. Fortunately, I have a plan. Get me out of this dress.”

Tom searched around the voluminous fabric. “There’s no zipper. How the hell did you get this on?”

“Block and tackle in the loading dock. Lift from the bottom.” She raised her arms up as Tom lifted the heavy dress over her and set it carefully to the side.

Kelly struck a catwalk pose. “Ta da!” She was, indeed, wearing a light gray strapless bra and bikini-style panties. Her long legs, formerly hidden by the floor-length dress, were covered in sheer white stockings, with gray ribbons winding in and out at the top serving as garters.

“Gorgeous,” Tom said.

She held the pose a moment longer, then reached back and undid the clasp of her bra. Her taut round breasts barely dropped when she took it off and threw it over to Tom. “Put it on,” she said. He grinned and wrapped it around his chest, doing up the hooks and spinning it around into its proper position. He grasped for the straps before he remembered, and she laughed.

“Habit,” he said. “I don’t usually wear strapless bras.”

“Me, either,” Kelly said, caressing her breasts. “These girls are just big enough to where the extra support is more comfortable.”

Tom stepped closer to kiss “the girls,” but she pressed a finger into his chest to hold him off. “You haven’t finished dressing yet,” she said.

He knelt down in front of her and grabbed the waistband of her panties, kissing along her taut belly and moving south as he slowly pulled them off of her. She had dark pubic hair cut into a narrow rectangle, a “treasure trail.” Tom kissed his way down and waited until she lifted one leg to step out of the panties, then licked her pussy lips fast. She yipped and hopped backwards.

“Sneak!” she yelled. “Just for that, I won’t let you wear the stockings. So there.” She stuck her tongue out at him. He mirrored her, turning it into a crude gesture, and she fanned herself. “Oh my. Promises, promises.”

He grinned and shucked off his pants and boxers, then stepped into the panties, slowly pulling them up his legs as he straightened. The top of his cock stuck out of the waistband, already glistening with pre-cum.

“Goddammit, they look better on you.” Kelly pouted. She stalked over to him with a slutty walk, hips swaying. She grabbed his cock through the thin fabric. “But this,” she murmured, “this I can work with.” She squatted down in front of Tom, licking and nibbling his cock, returning to the head often to lick away the beads of pre-cum swelling up. Her hands massaged his ass through the silky gray panties as she finally took him deep into her mouth, rolling her tongue around his cock as she sucked.

“Oh wow,” he said. “So good.” He let he continue until he felt the familiar tension build, then pulled her to stand. He didn’t want to cum yet. He kissed her deeply, his hands kneading her breasts, grabbing her hard ass, and sliding between her legs. She was already soaking wet.

He maneuvered her to where she could lie back on the weird couch thing and held her legs apart. He knelt down in front of her pussy, licking and sucking her clit. She gasped and moaned. He ran his tongue up and down, tracing her labia, pulling them gently between his teeth. Her hands wrapped in his hair. “Quit teasing and eat me!” she cried, pushing his face into her soaked slit.

Tom shoved his tongue deep into her cunt, driving her to her first orgasm. He rode the rhythms, slowing down as she recovered her breath.

“Oh my god,” Kelly panted. “Remind me to thank the Loftins. You’re good at that.”

“I’ll have you know this is one hundred percent natural talent.”

She snorted. He laughed. “No, you’re right; Anne is a very patient teacher.”

“I’m picking out ‘Thank You’ cards in my head until I can move again.”

“You don’t have to move.”

“I want to get on my hands and knees. I love doggystyle.”

“Absolutely not,” Tom said firmly.

“What’s wrong? Why not?”

“Because then you’d have to look at that fabric.”

She burst out laughing. “How chivalrous! My very own knight in shining lingerie!”

“Not that chivalrous; I can caveman with the best of them.” He stared her down. “Prepare to be fucked, Missy.”

“Yes, sir!”

Tom pulled the panties to one side, freeing his cock. He aimed it at the center of Kelly’s wet pussy, then drove forward hard. She gasped and clutched at his arms.

“Yes! Oh fuck me, Tom!”

He slid in and out of her fast, watching her tits bounce as he held onto her hips. Her stockinged legs wrapped around him, pulling him deeper and deeper with every thrust. It wasn’t long before they both came, crying out together. Tom collapsed onto his elbows above her. Her hard nipples just reached his chest, and he nuzzled into her cleavage briefly before kissing along her throat. Kelly was mumbling something.

“What’s that?” he said, pulling back a little.

Lots of ‘Thank You’ cards.”

He laughed. “Hmmm…you’ve already got the stockings. What are you doing tomorrow night?”

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 3


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