Eric smiled as he placed his suitcases on the guest bed. When his friend Elizabeth had asked him to house-sit for two weeks, he'd jumped at the chance. She lived in a huge house in a ritzy golf subdivision, right on the 18th hole, and he enjoyed the amenities he could never have afforded on his own. In addition, living with three roommates didn't give him many opportunities for any alone time. He could barely contain his anticipation as he unpacked the first suitcase. The one that held his regular things.
The second case was filled with "Stephanie's" outfits.
After a long shower in the marble bathroom, Eric chose a dark purple satin bustier with matching panties, sheer black thigh-highs with dark purple garters, and a pair of black three-inch "fuck me" pumps. He donned his red wig in contrast to the purple fabric, and carefully did his makeup at the vanity. A pair of breast prosthetics gave him an enviable 36C figure. He threw a black satin robe over the outfit and went into the gourmet kitchen to fix a light supper, singing along with the tunes pumped through hidden speakers.
After supper, Eric went out on the screened-in porch with a glass of wine to watch the sunset. It was Friday night, and he was looking forward to the rest of the weekend.
Whack!
A golf ball hit a tree in front of the porch and ricocheted into the shrubbery along the edge. A few moments later, two others landed on the fairway, far short of the green. Shortly thereafter, Eric heard the whine of two carts approaching on the small roadway that wound between the holes. Three men, obviously retired, were giving each other grief about their lousy golf skills. They stopped the carts and got out. Two stepped over to the fairway to continue the play, while the other looked around.
"It's over here," Eric called out, pointing to the bushes on the other side of the screen.
"Thank you, ma'am!" the duffer called out as he approached. Eric stifled a giggle.
The man drew closer, and Eric checked him out. Short, a little overweight. Probably going bald under the flat cap he wore, but sporting a thick mustache to make up for it. Piercing blue eyes shone out from within a nest of wrinkles, and a firm mouth without many smile lines. This was obviously a man whose business had been his life. A high-powered management type unsure what to do in his retirement.
"Appreciate the help," the man said, parting the greenery in search of the ball. "I really don't like this game, but my friends do." He chuckled without much humor.
"My pleasure," Eric said.
The man looked up, then, really noticing Eric for the first time. "Wow!" he said. "Hello! I'm Malcolm."
"Stephanie. Pleased to meet you."
"Same here. If I'd known you were waiting at the end, I'd have made those idiots skip the first seventeen holes."
Eric laughed. "I just got out here, so you would have had a long wait."
"Worth it," Malcolm said with a nod. He turned to his friends. "Cal! Jon! Come over and meet Stephanie!"
The other two men strolled over, pausing to put their clubs back in the bags strapped to the back of the carts. They were a little taller than Malcolm, carrying their weight in their bellies like older men do. Cal had light brown hair, still thick at his age, and was clean-shaven. He had clear brown eyes and a strong nose, with good cheekbones and a full mouth. Jon wore his dark hair a little longer than the others, and hadn't shaved in a couple of days. His bright green eyes lit up when they landed on Eric, and he smiled.
"What did you find, Malcolm?" he asked.
"This pretty lady sitting all by her lonesome out here, just waiting to help stray golfers," Malcolm replied, and they all laughed.
"Are you new to the neighborhood?" Cal asked.
"Just house-sitting for a friend," Eric replied. "I'm only here for two weeks."
"Well that's a shame," Jon said. "We only play on Fridays, so we'll miss out on your company."
"You don't have to miss out," Eric replied. "Come in and have some wine."
"I could do with some refreshment," Malcolm said. "Maybe even some wine, too." He winked at Eric.
Eric led the way back into the den, then went and got glasses for the three men as they chose seats. Jon and Cal sat on the couch in front of the windows, while Malcolm chose a recliner. Eric passed around the drinks, then sat in another recliner, facing his visitors. As they chatted, Eric was aware of how intently the other men were checking him out, their eyes darting to his legs, his bust, and his mouth. He made sure to shift in his seat often, letting his robe gape open in strategic places. He enjoyed the effect he was having on the older men, an effect evidenced by the bulges at the front of their pants.
"So how long have you gentlemen been retired?" Eric asked them.
"Ten years or so," Malcolm replied. The others nodded.
"Married?"
They all shook their heads. "I'm divorced," Malcolm said.
"Never tried it," Jon said.
"Widower," Cal said.
"I'm sorry to hear that," Eric offered.
"Thanks, but no need. She died thirty years ago. It was a marriage of convenience more than anything."
Malcolm laughed. "You mean, she got to spend your money and you got to keep fucking men."
"Well, yeah," Cal agreed. "Why'd your wife leave you again?"
"Because I wouldn't stop fucking men or give her enough money." He snorted and drank more of his wine.
"That's why I never married," Jon said. "Kept all of my money and could fuck who I wanted."
"And who was that?" Eric asked.
Jon grinned. "Men." They all laughed.
"Is that what you do when you're not golfing together?" Eric asked with a grin.
Malcolm nodded. "A lot more now that we're retired, yeah. That's how we three met originally, at swingers clubs and adult book stores. This was before the internet made it easier. And we're always on the lookout for new gurls to play with." He winked at Eric.
"But I don't know how to play golf," Eric said with a cocky grin.
"That's okay," Cal said, standing up and walking over. "There are two other holes that are much more fun." He leaned over and gave Eric a deep kiss with lots of tongue.
"Hell, yeah," Jon said, standing up and pulling off his shirt, revealing a white satin bra. He started working the buckle on his belt.
Malcolm rose from his chair and walked over. He reached down and undid the knot at the front of Eric's robe, spreading the thin fabric aside. "Damn, Stephanie! You look amazing!" His knelt between Eric's legs, and his hand massaged Eric's hard-on through the silky panties.
"Quit hogging that mouth, Cal," Jon interrupted. He was down to just bra and panties now, his cock tenting the front and leading the charge as he stepped to the other side of Eric's chair. Cal broke off the kiss and started undressing as Jon turned Eric's head towards him. Eric mouthed Jon's cock through his panties while the older man moaned.
In no time at all, all three golfers were undressed, showing off their sexy lingerie. Eric sucked on Jon's cock while jerking off Cal, switching whenever one of them got close to coming. In the meantime, Malcolm had pulled the purple panties aside to get at Eric's hard-on. His mustache tickled a little as he slurped up and down, and the nylon of his black lace bra rubbed against Eric's thighs.
Soon, Eric found himself on his hands and knees on the floor. Malcolm was behind him, fucking his tight asshole with strong strokes. Cal was lying underneath Eric, sucking Eric's cock as it jerked back and forth to Malcolm's rhythmic pushing. Jon stood in front of Eric, one hand on the back of Eric's head while Eric tongued and sucked his lovely cock. The three men rotated according to some system they'd worked out years before, and Eric was always the centerpiece, pierced at both ends and dribbling cum from front and back!
"Damn," he said during a breather. "I should have taken up golf long ago!" The three older men laughed and closed in again.
Enjoy older crossdressers? Me, too! If you liked this story, drop a line. Feedback always welcome, or just say hi! shannon.christophe@yahoo.com
A reminder: If you don't want to see Nifty filled up with ads, or disappear entirely, donate today! http://donate.nifty.org/donate.html