Crossdressingstories Novels & Stories

The fiery redhead model stood beside her, beautiful and confident, wearing only lingerie. Catherine looked Kane up and down. “So this is the detective you can’t stop fucking, he’s hot.” Vera pulled Kane into the bedroom. “Watch first.” Vera and Catherine kissed deeply, hands roaming each other’s bodies. They moved to the bed, where Vera pushed Catherine down and buried her face between the redhead’s legs. “Oh fuck, Vera,” Catherine moaned loudly, hips grinding against Vera’s tongue. “Eat my pussy just like that.” Kane watched, cock rock hard, as the two women devoured each other. Vera licked Catherine’s clit while fingering her, making the younger woman scream.

Mia's POV I couldn’t believe I was doing this again, but my pussy was already soaked just thinking about it. Lena and I showed up at Jake’s house party dressed like total cumsluts. I wore a tiny black micro-skirt that barely covered my ass and a sheer white crop top with no bra — my hard nipples clearly visible through the fabric. Lena had on an even sluttier red dress that hugged her big tits and ended right below her pussy. No panties for either of us. Our heels clicked loudly as we walked into the packed living room.

“Since we are going to get you panties and stockings, I think we’re going to get some bras too, and some wobbly-bobbly silicone breast pads.” After paying for the clothes we fitted at the counter, we left the shop and went to the lingerie department. Victor dragged me all around the store choosing sets and sets of bras and panties, and eye fitting them on me right in front of all the ladies. Believe it or not, even if I agreed to do this crossdressing thing, I was still capable of feeling embarrassed. Really. Victor picked a few sets of them with laces he liked, which match with the clothes we bought earlier. He pulled me to the fitting room and I tried everything on again.

It never fails to startle me how big his hands are. He’s dressed like a greaser so when he waggles his eyebrows at me, I pretend to swoon. Only I don’t have to pretend so much. “I guess nowadays we call it pleather. But back in the day…” I have chosen to dress as a ’70s house- wife, picking out a very Mrs. Kravitz ensemble à la “Bewitched.” “…they called it naugahyde.” His hand has meandered up my calf and is cupping the back of my thigh. Lightning stabs my skin, electricity skitters in my blood. He strokes me with a single finger and I fear I might come.

I smiled letting my lust sneak through. "Hold on," Timothy grinned. I was in trouble. "When I helped Cáel move in I saw he had a huge box full of women's clothes - not in his size. He's not a cross dresser." Gee - thanks Timothy, you right bastard. "What is a cross dresser?" Aya piped up. I groaned. "A cross dresser is a man who dresses up like a woman," Nikita provided. "A Drag Queen is a man who dresses up like a famous woman/actress/singer. A transvestite is a man who dresses like a woman because they want to be a woman."

Ezra had noticed this yet he fell hard for him. The problem was, Kendall only ever treated him like a bro. A roommate. A guy you'd share instant noodles with at midnight, borrow ten bucks or a benjamin from, a guy he'd occasionally elbow in the ribs during late-night Dirt 5 gaming sessions. Ezra got Kendall's attention sure—but never in the way he wanted. Kendall saw him only as plain, ordinary, Ezra. So, Ezra had done something stupid. Something very reckless. He’d created Maya—a female catfish Winstagram account, with photoshopped pictures of a Brunette girl from Stock photos. He had replied Kendall's story about Kafka being possibly better than Dostoyevsky.

The ropes bit into her skin in pretty patterns, and the sight made my nipples tighten against my dress. My breathing was getting shallow. I could feel myself getting wet, the slickness between my thighs impossible to ignore as we moved from scene to scene. Alexander pointed out different kinks: a St. Andrew’s cross with a man being caned until his ass glowed red, a couple engaged in sensual wax play where hot drips made the woman gasp and writhe, a quiet corner where a Domme had her submissive licking her boots while she casually chatted with friends. Every explanation he gave was calm, but his voice grew rougher with each one. I noticed the way his hand froze at my back, his fingers occasio

I was 22 years old after all. “I need him to see that I'm grown enough to handle the business.” I looked at Anthony's lips as I spoke, my hot breath washed against his face. His hand was still buried in my boxers. Even though I was a crossdresser, I preferred boxers to panties. “You are.” Anthony smiled. Leaning against me, he pressed his lips into mine, while his hand continued working on the bulge within my boxers. I could feel the fabric getting soaked with precum.

she gestured at me wildly “...this is illegal. How can one person be both hot and beautiful?!” “Well, as you can see,” Sebastian slung an arm over my shoulder, “with our Noah, anything’s possible.” “For once, I agree with you,” Penny said dramatically. She pulled out her phone and snapped a picture before I could react. “Hey! What are you...” I started. “This,” she said, shoving the phone in my face. My mouth dropped open. She had just posted the picture on our trip platform with the caption: Cross-dressing is the latest trend.

For the one man in the room who could write a single check that would keep my company from dying. I just didn’t know his face yet. The annual Voss Foundation Masquerade was the place where old money and new money fucked each other—literally and figuratively—behind silk and feathers and the polite fiction of anonymity. Everyone wore masks. Everyone pretended the silk made the sins lighter. I was here as Lena Cross, founder of a cybersecurity startup that needed a Series A or it would be dead by Christmas, and the biggest potential investor was rumored to be attending under a plain black half-mask.