Share and Share Alike
by Shannon
Tom made his way among the tables, stopping to check with each of the guests to make sure they were enjoying themselves. As the owner and head pastry chef of the catering company, he took pride in serving the best food, and always listened to complaints and suggestions. This gig was one of his regular events. Twice a year, the Oakwood Retirement Village hosted a big party for the residents. It was one of the newer developments where each resident had their own house rather than everyone staying in one building, and this dinner was just another way to help people meet their neighbors.
"How are you folks doing tonight? Everything good?" He smiled at the older couple at the table.
The man looked up with an angry frown on his face. "Are you our server? We've been waiting for the check!"
"Uh..." Tom began. "There isn't a check, sir. You..."
The man interrupted with a big smile and a laugh. "Just pulling your leg, son!"
The woman with him slapped his arm. "George. You're terrible." She smiled at him fondly, then turned it to Tom. "Ignore my husband. His sense of humor takes some getting used to."
Tom grinned back. "What can I say? You got me." He held out his hand. "Tom Clarke. I catered your meal this evening. I trust it was satisfactory?"
"George Loftin, and my wife Anne," the man said, shaking his hand. "It was damned delicious. That filet mignon just melted in my mouth. Perfect! Anne even liked it, and she's mostly vegetarian these days."
"It was quite good," Anne said, "but the veggie lasagna was better."
"Have you tried our desserts? I can guarantee that the crème brûlée is exceptional." He winked. "I made it."
"None for me, thanks," George said. "Already full."
"And I have to watch my girlish figure," Anne said. She turned that bright smile on again.
Tom liked her smile. As he looked further, there was a lot to like about Anne. She was a slender woman, very well dressed. Her long thick hair was red-going-to-silver, and hung down to frame her narrow face in artful waves. She had deep-set blue eyes, a slim nose, and wide lips painted dark red above a rounded chin. Sure, she had wrinkles, but they gave her face elegance rather than making it just look worn. Big pearl earrings matched the long triple strand of pearls around her neck. She wore a dark cranberry wrap and a gray dress, which she filled out very well.
"If you're going to keep staring at my wife like that, you'd better buy her dinner first."
Tom flushed guiltily, but there was something about the way George delivered the line that said he might not be all that upset. Summoning the nerve from who-knew-where, Tom looked George dead in the eye and spread his hands out to encompass all of the tables, waitstaff, and buffet line.
The older man roared with laughter. "Touché, son! Touché!" He raised his wineglass in salute, then turned to Anne. "I think you can add another one to your harem, dear." He chuckled.
"Our harem, you mean, and we left them all behind when we moved here. Still..." she cast an appraising eye over Tom, "we can always start a new one."
"Sure," George agreed. "We're not dead yet." He turned to Tom. "What do you say, son? Up for some adventure with the old folks?"
Tom checked his watch and smiled. "Does nine o'clock work for you?"
"Sounds good," George said. "Gives us time to get ready. Let's go, Anne." The older couple stood and joined arms. "173 Terrace Drive." Anne said as they passed, and patted Tom on the butt.
At least, he thought it was Anne.
Tom rang the bell at 9:00 on the dot. "Come on in, son!" George called. Tom walked into the small house, noting the tasteful furniture, the filled bookcases, and framed art on the walls. George and Anne were in the den. She sat on a sofa, while George poked at a fire in the fireplace. They were both still wearing the clothes they'd had on at dinner.
"Hello, again," Tom said.
" `Welcome to our parlor'," George quoted with a sly grin. "Get you a drink?"
"Scotch would be great," Tom said.
"Man after my own heart," George said, making the drink. "As well as my wife, apparently!" He laughed again.
"I'm just using her to get to you," Tom said, accepting the glass with a wink.
George looked surprised. "Well I never!" he stammered.
"You have so," Anne contradicted him with a smile. "And often."
"True," the older man agreed, and raised his glass. "Cheers!" He emptied the booze in one swallow.
Tom followed his lead, enjoying the smooth fire of the scotch.
"Let me get that for you," Anne said, rising from the couch. She walked over, high heels clattering on the hardwood floor. Tom held out the empty glass, but she grabbed his cock instead!
"Mmmm," she murmured. "Just as I'd hoped. Nice and thick." She put her other hand under Tom's chin and steered him into a deep kiss. He didn't even notice when George took the glass away, but he must have, because both of his hands were now filled with Anne's delectable ass. She moaned into his mouth as he squeezed, and pushed her big tits harder into his chest.
George came up behind his wife, reaching past her to grab Tom's hips and pull him forward, snuggling Anne between them both. Tom felt the older man's hard-on through his slacks. George reached up then and slipped the wrap off of Anne's shoulders. He tossed it onto a nearby chair, then started pulling her zipper down. Anne scooted back a little bit to allow the fabric to slide down. Her pale skin was covered with freckles, and she was wearing a semi-transparent white bra. Her big areolas and thick nipples barely showed through the fabric, and Tom bent down to nuzzle and lick them.
"Oh yes," Anne said. "Kiss Mama's titties. Mmmm. I love it." She wriggled her hips to drop the dress to the floor. Underneath, she wore white panties with lace at the edges and sheer black stockings. George held her hips as she carefully stepped out of the fabric, then he tossed it beside the wrap.
Tom stood up again to go back for more kisses. He felt George move behind him, then his hands reach around and work the buttons on his shirt. Tom shrugged the shirt off as George started on his belt and trousers, pulling them and his boxers down in one motion. Tom's cock sprang out, thick and hard. He ground it into Anne's panties, his pre-cum joining the wet spot that was already there. He kept kissing her hard while one hand pushed her ass towards him, and the other squeezed one of her perfect tits through the flimsy bra. Her pearls rattled in her deep cleavage as her chest heaved.
George squeezed up against Tom from behind. Tom felt some fabric against his bare back and ass, but it didn't feel like the suit George had been wearing. He turned far enough to see, and discovered that George was wearing the same lingerie as Anne!
"Wow!" Tom said. "That looks incredible on you!"
George winked. "We share everything," he said, and pulled Tom into a kiss every bit as deep as Anne's had been.
Tom sank into the kiss, and his hands were busy stroking George's cock, ass, and nipples through the thin material. George murmured and sighed. "Damn that feels good, son." He returned the attention, and it was Tom's turn to breathe faster.
A few moments later, both George and Anne were on their nylon-covered knees, sharing Tom's cock and the occasional deep kiss between them. Tom enjoyed the sensations for a while, then pulled Anne up. "This is driving me crazy," he said, reaching for her bra clasp as George continued to worship his cock. "I have to have these tits."
"Sure, baby," she said. "They're all for you."
"Hope not," came a muffled voice from Tom's crotch.
As the bra came off, Anne's heavy tits drooped towards her belly. They sagged, but they were still full and round. Her areolas and nipples were pale pink. She lifted them up in her hands, offering them to Tom. Her pearls clacked as she squeezed her breasts together. Tom bent down and took the left one in his mouth, rolling his tongue around the nipple as he sucked and gently bit. Then he moved to the right, repeating the attention.
"Oh yes!" she cried. "That's what Mama likes! Suck my tits! Make me wet!"
"Move over, son," George said. He took one of his wife's breasts in his mouth, leaving the other for Tom. The two men licked and sucked, kissed and pinched, as Anne pulled their heads tight against her chest.
"Mama's coming!" she panted, then arched her back and shuddered all over.
"Better get her back on the couch before she falls down, son" George said with a grin. Tom helped Anne sit down, then knelt in front of her. He grabbed the waistband of her panties, and she raised her hips to help. The thin white fabric slid down, and Anne spread her legs wider as they came off. Her swollen cunt lips, flushed a darker pink, stood out from a neatly trimmed red-haired pussy.
Tom rose up on his knees and bent forward. He dove into the slick snatch, pushing his tongue deep inside the older woman. She moaned and shook as he ate her out, and her finger worked her hard clit at the same time. Meanwhile, George worked Tom's cock from behind with slow strokes. After another orgasm, she scooted her hips to the edge of the sofa. "You really need to fuck Mama now," she demanded. She slapped George's hand away from Tom's cock and wrapped her stockinged legs around Tom's waist, pulling him into her to sink to the hilt. Her eyes rolled up as the thick cock filled her.
Tom started a slow rhythm, but then felt hands spreading his ass cheeks apart. George's cock pressed against his asshole.
"Just keep doing what you're doing, son," the older man said, and slowly pushed inside Tom, which drove him deeper into Anne's cunt. They worked out a good rhythm quickly, and the room was filled with gasps and moans.
Soon after, Tom felt his balls swelling. "I'm about to cum!" he said.
"Hang on a little bit longer, son!" George replied. "I'm almost there!" He leaned over Tom's back, plunging deeper. Tom could feel George's hard nipples even through the bra he was wearing.
"Fuck him good, George!" Anne shouted. "Fill his tight asshole with your hot cum while he fucks Mama's sloppy wet cunt!"
That did it. All three came together in huge orgasms, then collapsed in a sprawl, Anne on the couch, Tom and George on the floor.
"I, for one, need a cigarette," Tom mumbled. "Do you smoke after sex?"
"Don't know," Anne murmured, her eyes closed. "I wouldn't be surprised, though. George, be a dear and look for me."
"Look for yourself, you lazy bitch," George said. "I'm still recovering over here." He was on his back, his panties down to his knees where he'd pushed them to fuck Tom. He had a very satisfied smile on his face.
"Awww, poor thing," Anne said. She got up off of the couch and walked over to her husband. She knelt down, her knees to either side of his head, and slowly lowered her dripping snatch onto his face. "Don't just lie there; give Mama's pussy a good cleaning." She rocked back and forth as George licked and sucked.
"Mmmm," he said. "I can taste both of you. Delicious!" He kept going with more enthusiasm as Tom watched Anne's big tits sway with her movements.
"And you!" she said, pointing to Tom. "Come over here and suck this cock. He'll be hard again soon."
"Magic blue pill," George agreed.
"Shut up and eat me," she demanded.
"Yes, dear."
Tom crawled over and took the older man's cock entirely into his mouth. He started sucking and licking as he massaged his balls, too. In a very short time, he felt it swelling between his lips.
"Won't be a big load," George said, "but it'll still feel great to me, so don't worry."
"Feels good on this end, too," Tom said, and went back to sucking.
It didn't take long for George to have another orgasm. By then, Tom was ready to go again. He stood and stepped up to Anne, who was still sitting on George's face. "Mama needs a face fuck," he announced, and Anne nodded happily.
"Ah, the recuperative power of youth," George said. Or something close to it; it was hard to understand him.
Tom slid his cock into Anne's mouth and she clamped down with her lips. He held the back of her head and thrust back and forth rapidly until he felt the pressure building, then slipped out suddenly and sprayed hot ropes of cum over the husband and wife below him.
"I just finished cleaning this up!" George complained.
"We'll help this time, dear," Anne said, and the trio busied themselves with licking each other clean, swapping plenty of cummy kisses along the way.
Later, as they shared drinks and cigars on the patio, they made plans for their next rendezvous. Tom said that next time, he'd have a matching outfit, too.
"That'll be fun," George said, and Anne agreed.
"Our own personal dessert chef!" she said. "And our own personal dessert!"
Enjoy older crossdressers? Me, too! Feedback is always welcome. Send comments and suggestions, or just say hi! shannon.christophe@yahoo.com
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