My Girlfriend's Dad caught me wearing her clothes
Fictional Story. All characters are above the age of 18.
My girlfriend Sally (18) lived with her divorced dad Billy (40). It was a pretty new relationship but he didn't seem to care that I spent the night. She had to leave for work early in the morning and I was off that day. Her dad left shortly afterwards for his construction job. The second I heard both cars pull away, I dove straight into her closet like a kid in a candy store.
I’d been fantasizing about this for weeks. I liked to wear her clothes something about the soft fabrics and feminine cut made me feel so slutty and free. I rummaged through her drawers and picked out the sluttiest outfit I could find: a tiny pink crop top that barely reached below my nipples, a black pleated micro skirt that barely covered my ass, a pair of her laciest red thong panties, and thigh high white stockings with little bows at the top. I even slipped on one of her chokers and did my best with some of her lip gloss in the mirror. My heart was racing with excitement and nerves.
I grabbed my backpack and pulled out the thick, dildo I’d been hiding from her. Then I climbed onto Sally’s bed, put my headphones on with some loud porn playing rough daddy scenes where the girls got absolutely destroyed and lubed up the toy. I started slow at first, teasing my hole, but I quickly got lost in it. Soon I was on all fours, ass up, slamming the dildo deep into myself with long, greedy strokes. The skirt was flipped up over my back, the thong pulled aside, and I was moaning like a total whore into the pillow.
“Fuck yes… harder, Daddy…” I whimpered to myself, thrusting back onto the toy, completely lost in the fantasy. My cock was rock hard, leaking onto her sheets. I was going to town so hard that the bed was creaking and my moans were getting louder and louder.
Until I looked up.
There, standing in the doorway with his arms crossed, was Billy. Tall, broad shouldered, covered in a light sheen of sweat from the job site. His eyes were wide at first, then narrowed with pure hunger as they traveled over my dressed up body my ass still impaled on the dildo, skirt hiked up, glossy lips parted in shock.
I froze. The dildo slipped out of me as I scrambled to cover myself, but it was way too late.
Billy stepped inside and closed the door behind him with a soft click. “Forgot my fucking lunch,” he said, voice low and gravelly. “Heard some strange noises and thought maybe a burglar got in. But this…” He let out a dark chuckle, his gaze locked on me. “This is better than I could’ve imagined. My daughter’s little boyfriend all dolled up like a cheap fucktoy in her clothes.”
I tried to speak, but my voice came out shaky. “Billy……sir, please… this isn’t… I can explain ”
He cut me off by stepping closer, towering over the bed. “Explain? Look at you. Lip gloss. Stockings. That fat toy still shiny from your ass. You’re a secret little sissy, aren’t you?” His hand reached down and gripped my chin, forcing me to look up at him. “Here’s the deal, princess. If you want this to stay our dirty little secret if you don’t want me to call Sally right now and tell her exactly what her boyfriend was doing in her bed while she was at work you’re going to take care of me. Every inch. And you’re going to do it like the eager little girl you’re dressed as.”
My face burned with shame and twisted arousal. I nodded slowly.
“Good girl,” he growled. In one swift motion he grabbed me, flipped me onto my back, and pinned my wrists above my head with one strong hand. His other hand yanked the dildo completely away and tossed it aside. “That cheap toy’s got nothing on the real thing.”
He unzipped his work jeans and pulled out his cock. It was thick, veiny, and already rock hard noticeably bigger than the dildo. He shoved my legs wide apart, pushed the tiny skirt up around my waist, and rubbed the fat head of his cock against my slick, pre stretched hole.
“You want this secret kept?” he asked, teasing my entrance. “Then beg for it.”
“Please…” I whispered, voice trembling. “Please sir…... I’ll do anything. Just don’t tell her.”
He smirked and thrust forward, burying half his length inside me in one powerful stroke. I gasped loudly, back arching off the bed. The stretch was intense, overwhelming. He didn’t give me time to adjust he started fucking me with deep, heavy strokes, each one pushing deeper until his balls were slapping against my ass.
“Fuuuuck, that’s tight,” he groaned. “Been a while since I had a hole this eager. You like getting fucked in my daughter’s clothes, huh? You little slut.”
“Yes……fuck…… yes….. Daddy,” I moaned, the words slipping out as pleasure took over. He picked up speed, pounding me harder, the bed slamming against the wall with every thrust. His big hands gripped my hips, pulling me back onto his cock like I was just a toy for his aggression.
He leaned down, biting my neck hard enough to leave marks. “That’s right. Call me Daddy while I wreck this boy pussy. If you want this secret safe, you’re gonna moan like a whore for me every time. You’re gonna dress up pretty whenever she’s gone and let me use you however I want. Understood?”
I was nodding frantically, lost in the rhythm of his brutal thrusts. “Yes Daddy! I’ll be your secret girl… I’ll take your cock whenever you want… just please don’t tell Sally!”
Billy laughed darkly and flipped me over onto my stomach, yanking my ass up into the air. He slammed back in even deeper from behind, one hand fisting my hair while the other smacked my ass hard.
“Look at you taking it so well,” he grunted. “Moaning like a pornstar. Bet you’ve been dreaming about this.” His pace was relentless long, powerful strokes that made my eyes roll back. I was drooling onto the pillow, cock leaking constantly onto her skirt as he railed me.
He kept talking dirty the whole time, reinforcing the threat and the thrill. “You ever try to hide this again and I’ll show her pictures. But if you’re a good little cumdump for me… this stays between us. You’ll get fucked raw every chance we get.”
I came first hard shooting all over the bed without even touching myself, my hole clenching around his thick cock. Billy groaned at the feeling and fucked me through it, not slowing down for a second.
He kept going for what felt like forever, switching positions, using me however he wanted missionary while choking me lightly, then riding my face with his heavy balls before flipping me back over and pounding me into the mattress again. Every time I moaned or begged, he reminded me of the secret we now shared.
Finally, with a deep, animalistic growl, Billy buried himself to the hilt and came hard, flooding my insides with thick, hot loads. He stayed inside me for a long moment, panting, his hand gently stroking my thigh like he was claiming his new toy.
“Clean yourself up before she gets home,” he said as he pulled out, cum leaking down my thighs. “And be ready for next time she leaves early.”
He grabbed his lunch from the kitchen and left me lying there, dressed in his daughter’s ruined clothes, already wondering when he’d catch me again.