David looked at the clock. He had just enough time to finish getting ready.
He had moved here a year ago after getting a fantastic job offer. At thirty-six, he was finally earning a substantial salary. A few months later, he'd decided he was ready to buy a house, another first in his life. He'd always rented before, but now he wanted to build up some equity. His realtor, Allen Alders, had been very patient with all of David's questions and worrying and second-guessing. Allen had lived here for every one of his sixty-seven years and knew everybody. He got David a very good deal.
When the last of the paperwork was signed and the keys handed over, David invited Allen to dinner as a thank you and told him to pick the place. Allen suggested a very upscale Italian restaurant in a nearby city, and David agreed to meet him there the next evening.
Dinner was every bit as good as Allen had promised. David signed off on the check, and was amused to discover that the restaurant had applied the Senior Citizen discount to Allen's meal. He elected not to tell him. David had made a reservation at a nearby hotel because he'd expected to drink a lot more in celebration than he actually did. It was almost 10:30 before the men finished their meals, and Allen decided he'd do the same rather than drive home so late. As luck would have it, he was able to get the room next to David's. The two rooms shared a connecting door, and they assured the clerk that it was no problem at all. David picked up his overnight bag and headed to the elevator while Allen drove to a drugstore to get a razor, toothbrush, and other necessities.
When Allen returned, he started getting ready for bed, only to find that he had forgotten to buy toothpaste. He threw on his boxers and knocked on the connecting door to ask David if he could borrow some.
The cleaning staff evidently forgot to lock the door, because it swung open at his knock. He was astonished to see David standing in front of the dresser mirror wearing a wavy red wig, red lipstick, and a long black charmeuse nightgown. The silky fabric swirled around his ankles in a solid fall, and lace ran from the shoulders to the full cups of the bodice. Allen must have made a sound, because David turned, and it was obvious he had a raging hard-on.
Ten minutes later, Allen's boxers were around his ankles and his cock had lipstick prints on it. Ten minutes after that, he was balls deep in the younger man's ass, the pillow muffling David's--a.k.a. Siobhan's--moans of pleasure.
Since that night, Allen had stopped by David's house every couple of weeks. A natural sub, the boy always took good care of the older man.
David finished dressing and ran a brush over the coppery waves of his wig. A quick makeup check satisfied him, and he pursed red lips--the same shade he wore at the hotel; Allen insisted--and blew a kiss at his reflection. When the knock came, he hurried to open the door.
Allen had obviously come straight from work, because he had his business suit on. He smiled at David.
"Hey, sweet girl."
"Hi," David replied. "Come in."
Allen stepped into the house, kissed David's cheek, and looked him up and down. He was wearing a gray button-up blouse, coffee-colored straight skirt, and sheer stockings. His red heels matched his lipstick.
"Very pretty," Allen said, and David preened a little before helping the older man out of his suit jacket. Allen pulled off his tie and handed it to David, who folded it neatly and put it in the jacket pocket.
"How about a drink, babe?" Allen asked, and David went into the kitchen to make it. While he did, Allen walked to the back bedroom and started undressing. By the time David arrived with his drink, he was completely naked. David handed him the glass and dropped to his knees. As Allen sipped the whiskey, David gently took his cock into his mouth and began sucking slowly and smoothly, with plenty of tongue action. He loved feeling Allen's dick swell up in his mouth, which didn't take long at all.
"Yeah," Allen murmured. "That feels good. Did you miss me?"
"Mmmm-hmmm," David hummed. He kept licking up and down the shaft of the hard cock in his mouth. He made sure Allen could see, because he liked to watch his cock slip between David's painted lips.
David heard the glass being set on the nightstand, and his anticipation rose. He absolutely loved this next part. Sure enough, he felt Allen's hand on the back of his head as the older man started to control the rhythm of the blowjob. No longer passive, he shifted his hips back and forth, sliding his wet cock in and out. "You like that, little girl?" he asked, and David nodded as best he could. "Such a pretty mouth, all warm and red. I love fucking it."
"Me too," David managed to get out.
"That's because you're a cocksucking whore," Allen said, "aren't you?"
David slipped off the older man's dick long enough to answer. "Yes. I'm your cocksucking whore."
"Good girl," Allen said, and pulled David's head back onto his hard-on. He pumped in and out of David's mouth a little longer, then slowly pulled out as the young man licked every inch.
Allen walked over to the bed and sat, leaning back on his arms. "Stand up," he said, and David complied. The older man jerked his chin at David's outfit. "What are you hiding under there, little girl? Something I'll like?"
"Yes," David said.
Allen waited a moment. "Well don't tease me, bitch."
David reached up and began undoing the buttons of his blouse. When he slipped it off, it revealed a shiny teal bra accented with lace along the cups.
"Ooooh," Allen said. "Pretty tits."
"Thank you." David reached behind to unzip the skirt, and it dropped to the floor. His panties matched the bra, and his stockings came up to mid-thigh. He carefully stepped out of the fabric and moved to stand in front of Allen in his heels and lingerie.
"Very nice," Allen said. "Very sexy."
"I was sure you'd like it."
"You know my tastes."
"I love your tastes."
"Then get down and prove it, little girl." He spread his legs further apart, and David knelt between them.
"Hey," Allen continued. David looked up.
"Make it sloppy."
The young man grinned and set to with a will, moving faster and looser than before. Allen's dick became wet with saliva, and more drooled down David's chin to drip on the sheets. He could taste Allen's pre-cum mixed in, and paid extra attention to the head of the older man's cock.
Allen loved watching a half naked girl go down on him so enthusiastically, but when he knew he was getting close, he told David to stop. "I want to fuck you," he said.
David climbed onto the bed and got on his hands and knees, sticking his ass in the air. David lightly smacked a cheek. "No. On your back." The younger man rolled over as ordered, and Allen got between his legs, caressing the smooth nylon of the stockings. He lifted David's legs and scooted closer. David felt the older man's cock rubbing against his ass, and pulled his panties to one side.
"So eager. You want this, whore? David nodded. "What was that? I didn't hear you."
"Yes."
"Yes, what?"
"Fuck me, Daddy," David panted. "Please. I need it. Fuck your little girl."
Allen got into position and slowly pushed his cock into David's tight asshole. The younger man moaned as he was filled up. "Yes," he said. "Like that."
Allen settled David's legs on his shoulders. Seeing his nylon-covered legs in the air like that, feeling warm hands around his ankles, was a big turn-on for the younger man.
They gradually built up into a good rhythm. Allen's cock sank to the hilt on every stroke, and David couldn't get enough. He moved his legs down and used his heels to pull the older man closer.
"Oh, Daddy! Feels so good. Give me that hard cock. Yes!"
Allen pulled David's hips towards him, trying to get deeper. "Take it all, you fucking slut," he snarled.
"A slut for you! Pound my cunt! Use me!"
Allen let himself go, grunting as he unloaded spurt after spurt of hot cum, filling David's ass. The younger man reveled in feeling Allen's cock throb and pulse inside him.
They finally separated and lay beside each other, panting as the sweat ran off of them. When they had caught their breath again, Allen turned to the younger man.
"Did you cum?"
"Not yet."
"Good. I want to watch you get yourself off."
David reached inside his panties and pulled out his cock. As he started stroking, Allen slid his hand inside the young man's bra to play with his nipples. As worked up as Allen had gotten him, it didn't take long for him to shoot ropy cum all over himself.
"Feel good?" Allen asked.
"Yes."
"Good. Let's go shower. Then you can put on that nightgown I got you and we'll get some sleep."
"Sounds good."
Allen took David's chin and turned his head towards him. He leaned over and gave the younger man a deep, deep kiss.
"My pretty little girl," he said. "My sweet Siobhan."
"Always," David agreed.
Enjoy older crossdressers? Me, too! Feedback is always welcome, or just say hi! Send comments, suggestions, or sexy selfies to shannon.christophe@yahoo.com
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