Crossdresser Stories Novels & Stories

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."

Crossdresser has an out-of-body sexual experience. Enjoy.. ***** My name is Rich and I am a crossdresser. I would prefer to be a transgender, but at this point in my life--married with two grown kids and a grandchild--it's just not in the cards for me. That doesn't stop me from dreaming, however. Several years ago, my wife came home unexpectedly and caught me in my women's clothes. She freaked out and demanded that I get counseling. I truly love Meg, and in order to save our marriage, I agreed.

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.

At this moment, Alex walked out after dispelling the spell formation. After asking around, everyone did not have any men’s clothes. The corpses on the ground had them, but all of them were smeared with blood. Alex did not want to wear those clothes either. In the end, Juliette took out a long dress. “Do you want this? I only have this.” ‘Cross-dressing?’ Alex forced a smile and accepted it. ‘A cross-dress is more powerful than a king’s new outfit!’ After wearing the long dress, he really looked a little coy.

“Actually, I did crossdress before when I was young. My mom wanted a daughter, but it turned out that I was a boy. Therefore, she decided to raise me like a daughter. “When I started to learn how to walk, my mom took advantage of the fact that I couldn’t resist and put me in dresses during summer. She even let my hair grow long and really treated me as a daughter.” Elisa was interested. She smiled. “I never heard of this before.” “It’s my embarrassing past. How could I let you know?” “How long did you wear dresses for? Didn’t your family oppose the idea?”

“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 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.

Kinks: CNC (Consensual Non-Consent), kidnapping, rough sex, being overpowered, degradation + praise, being used, forced orgasms, being claimed/possessed. She hesitated for a long time before hitting “match.” That same night, she matched with someone. Damien. His profile was simple: Damien Cross, 34 Kinks: CNC, kidnapping/roleplay, heavy dominance, ownership, rough sex, breeding talk, marking, aftercare. They started chatting. At first, it was cautious. Then it became intense. Damien: You said you like being taken against your will. How real do you want it to feel? Elena: As real as possible. I want to be scared. I want to feel like I don’t have a choice… but I also want a safe word.

My nose wrinkled in disgust at Ryder’s fake responses, my lips sealing once again over my cup of tea before speaking. “But what about cross-dressers? I recall you weren’t too fond of them.” Ryder’s complexion darkened, his fists clenching so hard his knuckled turned white. I sipped on my tea. “Saying I am not too fond of cross-dressers would be hypocritical as I am the one who buys my little brother’s skirts and make up, Carter.” The tea suddenly scraped against my throat, making me cough vehemently. My dad stretched on his chair, hitting my back twice with his palm.

So, Over the next couple of years, I started cross dressing & playing with big black toys, until I just couldn't take it no more. Then I found the M4T personals on Craigslist & quickly hooked up with another Big Black Cock, who fucked my now totally broke in ass pussy. Over the next few years I hooked up with another 10 Big Black Cock's, who I dressed up all sexy for & had them just fuck my ass pussy, with some of them even cumming all up in me too.