Panty Sissy Meets Big Bob

Harold’s knees ached as he locked the stall door in the rest stop men’s room off the interstate. At sixty-three, divorced three years and living alone in a quiet condo, he had long since stopped pretending the soft lace panties under his khaki slacks were just a private eccentricity. They were the only thing that still made his cock twitch with honest life. He sat, pants around his ankles, the pale pink satin and white lace cupping his shaved balls and half-hard dick, when he saw the note taped to the inside of the door.

The handwriting was thick, masculine, almost crude: “attention panty loving man contact Big Bob” followed by an email address scrawled in the same bold ink. Harold’s breath caught. His fingers trembled as he traced the words. For decades he had hidden this hunger—first from his wife, then from every empty night since the divorce—craving the full homosexual experience he had never dared take. The idea of another man’s hands on these panties, another man’s cock pushing into him, made his hole clench and his mouth water. He tore the note free, folded it carefully into his wallet, and finished as quickly as his shaking hands allowed.

The drive home was pure agony. Every red light stretched forever. In the condo he stripped naked except for the pink panties, sat at the laptop, and typed with one hand while the other rubbed the damp silk over his leaking cock.

“Dear Big Bob,” he wrote, “I found your note. I’m a divorced senior, sixty-three, and I’ve worn panties in secret for years. I’m a sissy—I love the feel of lace and satin against my skin—but I’ve never been with a man. Never touched a cock that wasn’t my own. Tonight I finally want the full homosexual experience I’ve been craving. If you’ll have a nervous panty-wearing faggot like me, please write back. Harold.”

He hit send before he could delete it. The reply arrived in under four minutes.

“Harold, you sweet little panty slut. Big Bob here, fifty-eight, thick, hung, and I love turning shy sissy boys into dripping fucktoys. Come to my apartment tonight. Address below. Wear your prettiest panties under loose clothes. I’ll open the door, drop your pants, and inspect every inch of lace. Be here by nine. Don’t keep me waiting, good little sissy.”

Harold’s cock jerked hard inside the pink satin. He showered, reapplied lotion so his skin felt soft, and chose a pair of black sheer panties with a tiny red bow at the front—so sheer his cock and balls were clearly outlined. Over them he pulled dark slacks and a button-down shirt. The drive across town felt like floating. His hole kept fluttering open and closed with every heartbeat.

Big Bob’s apartment was on the second floor of a quiet brick building. The door opened before Harold could knock twice. The man filling the frame was broad-shouldered, silver-haired at the temples, with a thick chest under a tight black T-shirt and jeans that strained around a heavy bulge. His smile was wolfish and kind at the same time.

“There’s my nervous panty sissy,” Big Bob said, voice low and gravelly. “Get inside.”

Harold stepped in. The door clicked shut. Before he could speak, Big Bob’s big hands were on his belt, yanking it open, shoving the slacks down to his knees. The black sheer panties came into full view, Harold’s cock already tenting the thin fabric and leaving a wet spot.

“Fuck, look at that,” Big Bob murmured, circling him slowly. “Pretty little sissy cock all locked up in lace. Turn around. Let me see that ass.”