Lose Yourself

You kissed your wife goodbye in the driveway, her soft lips lingering on yours as she held your face gently. The faint scent of her vanilla shampoo and the warmth of her body pressed against you made your chest tighten with guilt. “Come back to me soon, babe. I hate these longer trips,” she whispered, her voice full of genuine love and longing. You told her you loved her, climbed into the SUV, and drove away, watching her wave in the rearview mirror until she disappeared.But the second you hit the highway, the mask slipped completely. Your itty bitty clitty was already leaking steadily into your panties, the small plug in your ass shifting with every bump in the road. Four nights. Three days. Plenty of time to go deeper than ever before.

Night 1 – ManRyan was waiting for you in the dimly lit hotel bar, his tall, muscular frame impossible to miss. The moment you entered his room, the door barely clicked shut before he grabbed you by the shirt and shoved you roughly against the wall. His hot breath brushed your ear as he growled, “Strip, sissy. Show me what a married conservative slut looks like under those clothes.”Your hands trembled with nerves and excitement as you obeyed. When he saw the pink panties and the small jeweled plug already nestled deep in your ass, he let out a low, mocking laugh that sent shivers down your spine.“Fuck, you really came prepared like a **** little whore.” He hooked two thick fingers into the waistband of your panties and yanked them down. Then he gripped the base of the plug and pulled it out slowly, the wet, obscene pop echoing in the room. Your hole twitched and winked at the sudden emptiness, already craving to be filled.He spat thickly on his rock-hard 7-inch cock, the fat, veiny head glistening under the lamp light.

Without warning, he pressed it against your hole and **** it inside you in one long, brutal thrust. The stretch was intense a burning, tearing pressure that made your eyes water and your breath catch in your throat. You gasped loudly as he sank deeper, every thick inch dragging roughly against your sensitive inner walls. The heavy, masculine musk of his sweat mixed with cologne filled your nose as he pressed his solid, powerful body against your back.

Then he started pounding you mercilessly.The wet, rhythmic slap-slap-slap of his hips slamming against your ass filled the room. Every powerful thrust slammed directly into your prostate, sending white-hot jolts of overwhelming pleasure through your caged clitty. Your tiny locked dicklet leaked constantly, dripping onto the carpet as he used you like a cheap fucktoy.

“Take that dick, you pathetic married bitch,” he growled, gripping your hips hard enough to leave bruises. “This is what you really are out here selling conservative values all day while secretly begging for real cock at night.”The constant hammering against your prostate became too much. Your itty bitty clitty spasmed wildly inside the cage, spurting weak, watery ropes onto the floor as you moaned like a broken whore, voice cracking pathetically. Ryan laughed darkly and kept railing you through your orgasm, his heavy balls slapping wetly against you until he finally buried himself to the hilt and unloaded. You felt every thick, pulsing rope as he flooded your guts with hot, sticky cum, the warmth spreading deep inside you.He pulled out slowly, watching with satisfaction as his thick load began to leak from your gaping, twitching hole. “Keep those panties on,” he ordered. “I want you walking around tomorrow with my cum still inside you.”

The next night after your first full day of sales for this trip, you went much further. In your hotel room, you spent nearly an hour transforming into “Kylie.” The blonde wig felt surprisingly natural. The short black dress hugged your body tightly, the hem barely covering your ass. Thigh-high stockings whispered against your smooth skin as you slipped on the heels.

Full makeup smoky eyes, glossy pink lips completed the look.

Ryan brought his friend Derek. Both men’s eyes widened with raw lust when they saw you.“God damn,” Derek laughed, grabbing your ass roughly, his strong fingers digging into the soft flesh. “You really went full slut tonight.”They didn’t waste time. They pushed you down onto your knees on the rough carpet. The salty, musky taste of their precum coated your tongue as you sucked both their cocks eagerly alternating between them, gagging and drooling messily while they slapped their heavy, veiny shafts across your face. The wet gluck-gluck-gluck sounds of you **** on them filled the room as saliva dripped down your chin onto your fake tits.They bent you over the bed. Derek went first, slamming his cock into your already-sore ass with one brutal thrust. The burning stretch and deep fullness made you cry out around Ryan’s cock in your mouth. They spit-roasted you mercilessly, switching positions every few minutes. The wet slap of skin, your muffled **** moans, and their grunts created a filthy, intoxicating symphony.

They eventually double-penetrated your ass both cocks stretching you wider than you thought possible. The intense burn mixed with mind-melting prostate pressure made your eyes roll back. Sweat poured down your back as they pounded you senseless. You came hands-free twice, whimpering pathetically as weak spurts leaked from your caged clitty onto the sheets while they laughed and kept destroying you.When they finally came, they flooded your ass with load after thick load, the hot cum overflowing and running down your thighs in sticky rivers. They made you push it out onto the floor and lick every drop up like a good girl, the salty-bitter taste coating your tongue and lips.

For the final night you stopped pretending entirely. You went full sissy for three men. You wore a pink maid outfit that barely covered your ass, full makeup, heels, and your smallest cage. They passed you around like a cheap, disposable toy in one of their suites.You sucked all three cocks eagerly, the heavy, musky scent of their balls filling your nose as you gagged and drooled messily. You ate their asses deeply, pushing your tongue inside while they stroked themselves and laughed at how eager you were. The slightly bitter, masculine taste lingered on your tongue.Then they took turns destroying your hole. One fucked your throat while another railed your ass, the wet gluck-gluck-gluck and slap-slap-slap sounds obscene and loud. They switched constantly, using every one of your holes without mercy. At one point all three took turns double-penetrating your ass, stretching you to your absolute limit. The burning fullness was overwhelming. Sweat poured down your body as they pounded you senseless, the thick scent of sex and male sweat heavy in the air.You came three times hands-free, each orgasm weaker and more pathetic than the last, your tiny clitty spurting helplessly inside the cage while they laughed and mocked your leaking, ruined state.The night ended with all three of them standing over you, jerking their cocks until they painted your face, chest, and maid outfit with thick, heavy ropes of warm, sticky cum. The salty taste coated your tongue and lips as you lay there, trembling and used, ass gaping and leaking profusely onto the sheets.

The drive home the next day was quiet. Your ass still ached with every bump in the road, a constant reminder of how thoroughly you had been used. Your mind was spinning with shame, pleasure, and dark excitement.

You had crossed another major line. Not just trans women anymore real men. Multiple men. Dressed like a complete sissy while they used you without mercy.You still loved your wife. You still wanted to be the man she married.