Teenage Crossdressing Stories Novels & Stories

Kristen rubbed at her twat, wondering what she should write next. There's that D&D game coming up, she thought. My best friend will be over. Mmm, what if it became naughty? >>>>>>>>>>> Virgin's Naughty Fantasy Dream Kristen Miller was hanging out with her friend, thinking about that next naughty story she wanted to write in her journal. That leather-bound one she had found at the Dollar Store for a steal. She had written three so far. Three naughty stories. This evening, she sat on the couch with her friend Natalie while in the dining room, which was just to the right, her older brother Carter held his weekly D&D game. The guys were off to rescue an elven princess from an ogre.

“Stress?” I could tell from the logos and colors of the paper bags that they weren’t for men. My cousin was gay, and he was proud of it, but ever since, he never liked crossdressing. He would splurge on expensive clothes, shoes, perfume, and accessories, joking he was too gay that he wanted to pamper himself with worldly possessions. I never believed him because he would sell them at the end of the year, put the limited-edition items on auction, and the money he earned from it would be donated to his favorite charities. “You change your preference now.” My lips curved into a smile as I teased Bob when he didn’t answer.

I can literally feel it messing with my head already. “What’s the deal with you?” I snap. “Are you a girl trapped in a boy’s body, or a transvestite, or, I don’t know, a transsexual?” He chuckles. “Oh sweetie, it’s all just one big fucked up mess to you, right? Don’t worry, I’m not trapped anywhere. It’s just ‘Fake Drug’ used to be some serious gender-benders themselves. Have you heard their lyrics? And the front man used to perform in dresses sometimes when they were younger, and he was smoking h-o-t in them. Rest assured, I won’t be the only cross-dresser in the crowd.”

The moment the door clicked shut behind us, she shoved me against a stack of boxes and ripped my dress completely off, leaving me in just my heels. “On your back. Legs spread wide,” she commanded. I obeyed instantly, lying back on a wide padded bench, spreading my thighs like a total slut. My shaved, soaked pussy was on full display, swollen and dripping. Lena took off her jeans completely, revealing the thick strap-on harness. Then she pulled something from her pocket — a long silk scarf. “Hands above your head,” she said. I raised my arms and she tied my wrists tightly together, then secured them to a metal bar above the bench. I was completely helpless now, tied up and naked for my best f

I snuck out at night, didn’t come home for days at a time, skipped school, stole clothes and makeup from the mall, smoked pot, and drank anything I could get my hands on. Playing up my bad girl image, I modeled myself after Bettie Page, dying my brown hair a deep blue-black, wearing thick bangs, keeping my skin pale and my lipstick deep red. Skintight clothes paired with black or red patent leather shoes completed the look. But it was just a sexy look. For all of the attention I received from boys, the kissing and pawing and fumbling in the dark, I never let things get out of control. Once, I let an older boy put his hand down my pants, but his probing fingers hurt, so I stopped him after a

I, Audace, have always been a lover of the finer things in life. My passion for the Belle Époque era has led me to cultivate a refined taste for exquisite cuisine, elegant attire, and, of course, the most exquisite pleasures of the flesh. As a life coach and a cross-dresser, I've found that my unique perspective on life has allowed me to create a niche for myself in the world of sexual liberation.

"A young woman vanishes without a trace. No evidence. No leads. As if she simply... ceased to exist." "The story fascinated me. I dug deeper, trying to find the truth behind the disappearance — until I came across a novel." My body went rigid. "What did you just say? A novel?" "The world we're in right now — it's a novel. I stumbled into it the same way you did. That's when I realized you didn't just disappear. You crossed over, just like me." "I've been watching you for a while. Everything about you confirmed it — you're the woman who vanished."

Except this candy store sold lace thongs and overpriced pajama sets. While I went for simple cotton briefs and a few comfy options in neutral colors, he was holding up red lace, purple silk, and—oh Gosh—a literal body chain. “Please tell me this isn’t even for wearing,” I said, horrified. “I mean, not in public,” he grinned. “Caden.” “I’m helping!” I squinted at him. “This isn’t help. This is foreplay disguised as capitalism.” He winks. “Exactly.” Eventually, I let him toss a few into the basket, because if this man survived swimwear, I could survive watching him giggle like a schoolboy while holding a sheer teddy that had no business existing in a family mall.

The animalistic sound had jerked me back into my surroundings, and I’d become aware of the sudden tension emitting from him toward one of the other teenagers, whose eyes had been roaming over me from the top of my head to my bare feet. As the other guy had gazed at me, I'd raised my arms, covering my braless breasts, which, too late, I had realized were way the hell too defined in the small summer top I’d been wearing and did little to cover their bare state. A smirk had slid across the teen’s lips at my action and letting out a low whistle, he’d turned toward Nathan. “Damn, Nate! No wonder you sold your soul to the devil; if I had pussy like that I’d have done the same thing!”

Christmas is only a few days away. ‘Well, I dildoed up.’ ‘You what?’ ‘Bought some strap-on stuff.’ ‘You are crimson.’ ‘Are you surprised?’ I squeaked. ‘And you look as though you have a hard-on.’ ‘Are you surprised?’ he growled and crossed his legs. ‘So, what happened?’ ‘I met him in a no-lights LGBT club. I pretended to be late, and while he was waiting, picked him up, as a bloke, seduced him, and him thinking I was a bloke, I took it up the – you know.’