Brian yawned as he looked at the phone mounted on his dash. It was 10:23 p.m., and he was making his last delivery of the night. The GPS said he was five minutes away.
Brian's day job as a stock clerk didn't pay a lot, so he'd taken this part-time gig to help pay bills. It also helped him learn his way around, since he'd only been living here a couple of months. Most customers were surprised when a 42-year-old man showed up at the door with their order, rather than some pimply-faced, bored teenager. He chuckled as he thought about how surprised the customers would really be if they knew his secret.
The GPS guided him through the last few turns down residential streets, until he was at the last house on the block. It was a modest ranch set far back on a large plot of land, a goodly distance away from the closest neighbor. The yard had a short hedge planted around the edge, enclosing a well-manicured lawn. Brian turned into the driveway and stopped in front of a double garage. A stone walkway led to the front door, and he balanced the pizza box as he carefully made his way along the path and up the steps. He rang the doorbell.
"Oh! Uh...just a second!" a voice called out from inside. A few moments later, the dark oak door opened to reveal an older man in a worn brown terrycloth robe, belted at the waist. He was probably in his sixties, with thinning salt-and-pepper hair cut short, brown eyes, a wide mouth, and a square chin.
"Sorry!" the man said. "I lost track of the time." Behind him, in what was presumably a den, the sound of moaning made it clear what had occupied his attention. The man blushed a little bit. "Thought I'd paused that," he muttered. "Sorry."
Brian smiled. What the customers did in their own homes was no business of his. He pulled the pizza out of the insulated carrying case. "I have a mushroom-extra-cheese for a Mr. Bailey. Correct?"
The man nodded. "That's me. Let me get my wallet." He ducked back into the den--Brian was amused when the moaning stopped--and reappeared with cash in hand. He held it out. "Here you are."
Brian handed over the pizza box and went to take the cash, but they fumbled the exchange and the bills fluttered to the floor.
"Oh drat!" said Mr. Bailey.
"No problem," Brian said. "Happens all the time. I'll get it." He bent down to retrieve the money.
And that's when he noticed.
Mr. Bailey's robe was ankle length, but he wasn't wearing slippers. Instead, his feet were encased in sheer red nylon.
Brian picked up the money and stood up. When he looked at Mr. Bailey, the older man knew he'd seen. The blush was starting again, almost the same shade as the hosiery he was wearing. "Um..." he began. "I can explain."
Brian smiled. "No need," he said. He pulled the collar of his "Slice o' Heaven" t-shirt to the side, revealing the strap of his own bra.
Mr. Bailey's eyes went wide. "You like to dress, too?"
"Ever since I was a teenager," Brian explained.
"Same here!" the older man said. "It's nice to meet another crossdresser." He juggled the pizza box and held out his hand. "Julie," he said, and winked.
"Crystal. Nice to meet you, too." Brian shook his hand and grinned.
"Well I'm sure you have other deliveries to make, so..."
"Actually, you were my last one of the night, and tomorrow's my day off."
"Oh! Well in that case, would you like to come in?"
"Sure!" Brian stepped into the entry hall and shut the door.
Mr. Bailey--Julie--led the way into the den. On the screen, a man dressed as a maid was bent over a chair. The movie had been paused just as a transsexual woman in thigh-highs and heels was about to fuck his ass. "One of my favorites," he said with a grin.
Brian laughed. "I haven't seen that one, but I like it so far!"
Mr. Bailey set the pizza on the coffee table and sat down on the couch. He motioned. "Please! Sit!" He reached for the remote as Brian occupied the other end of the sofa. The movie started up again, and Mr. Bailey opened the box, grabbing a slice and digging in. He gestured. "Hungry?"
"Goodness, no," Brian said. "I got tired of pizza about two weeks into this job." He laughed.
Mr. Bailey nodded. "I can understand that. I eat more than I should, but I hate to cook. It's easier to just order something." He pulled a beer can off a ring and handed it to Brian, who cracked it open.
They sat together, drinking and watching the television. The first video ended and another started, this time with three crossdressers meeting in a bar. As the action heated up onscreen, Mr. Bailey's hand reached down, ducking between the edges of the robe to rub his crotch.
"Want some help with that?" Brian offered with a wink.
"Oh yes. That would be lovely."
Brian rose from his seat and pulled the older man up, moving them to stand between the coffee table and the television. He reached for the belt of the robe and undid the simple knot. He pulled it open to see the rest of the outfit. The elder man was wearing a bright red bra, matching corset and panties, and thigh-high stockings. His cock wasn't too big, but it strained against the thin fabric.
"Very nice outfit, Julie," Brian said.
"Thank you, Crystal. What are you wearing?"
Brian shucked out of his work clothes, revealing his wine red bra and panty set, a black garter belt, and black stockings. The bra was embroidered with black lace on the cups, and the panties had a lace panel at the front. His cock was just barely visible through the lace, but the bulge was very evident.
"Oh my," Mr. Bailey said. "You are a sight, darling."
"Thank you, sweetie."
They admired each other for a moment, then Brian smiled. "You wanted some help?" he prompted.
The older crossdresser nodded. "I'd enjoy that very much."
Brian walked around Mr. Bailey, running his hand along his chest, arms, and back. He leaned in close, pressing his cock against the older man's ass.
"Wonderful," Mr. Bailey sighed.
Brian reached forward, massaging the older man's breasts through his bra, tracing his hard nipples.
"Mmmm," he said. "I love having my tits played with."
"And I like this great ass, Julie." Brian pressed harder against the silky panties, rubbing his cock up and down.
"Take it, Crystal; it's yours."
Brian slid the red nylon down Mr. Bailey's legs, revealing an ass that, while no longer taut with youth, was still shapely. He sucked one of his fingers and began probing the tight asshole, gently working his way inside.
"Oh yes, darling. Feels so good in my ass. More!"
Brian pulled off his own panties, releasing his large cock. He maneuvered Mr. Bailey over to where he could brace himself on the back of the couch, then spread his ass cheeks as the head of his cock, wet with pre-cum, probed. He sank in slowly, inch by inch, until he was fully sheathed in the old man's boy-pussy.
"So much better than my dildo," Mr. Bailey sighed. "Fuck me, Crystal!"
Brian pumped his hips slowly. One hand reached around to play with Mr. Bailey's nipple under the satiny bra.
"Oh god, yes!" The older man cried out.
Brian pumped faster, feeling the pressure building up in his balls. His hand dropped lower, grasping Mr. Bailey's cock, jerking him off in time with the fucking he was getting.
"I'm gonna cum!" he said.
"Me, too!" Brian gasped.
"Fill me up, Crystal! Flood my asshole with your hot cum!"
"Oh, Julie!"
The two men came at the same time, collapsing breathless across the couch. After a few moments, Brian pulled out of the older man's ass and stood up. "You felt great!" he said.
"I haven't been fucked like that in a long time," Mr. Bailey said, turning to face Brian. "You were wonderful, Crystal." He gave the younger man a deep kiss. "Can you stay tonight? I have some nightgowns that would fit you."
"I'd like that a lot, Julie. Sure!"
"Good. And then I'll have a chance to fuck you, too!"
"Oooh...I can't wait to feel your cock inside me."
"One thing's for sure," Mr. Bailey chuckled as they headed to the bedroom, "I'll be ordering a lot more pizza from now on!"
Enjoy older crossdressers? Me, too! If you liked this story, drop a line. Feedback always welcome, or just say hi! shannon.christophe@yahoo.com
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