Cross-Dresser Story: Dressed and Desired

The Dare She Gave Me

I am Jamie, I am thirty, and I am a man who loves to dress, and for a long time I only did it alone, behind a locked bedroom door, in clothes I hid in a drawer. Lena is twenty-nine, an adult woman, my partner, and she found my dress one evening and did not make a joke of it. She held it up, she smiled, and she dared me to wear it for her, properly, that night, with makeup and heels and everything, and to let her see me the way I saw myself when I was alone. I was nervous, I was hard, and I said yes before I could talk myself out of it.

Lena took charge of the dare like she had been waiting for it. She laid the dress out on our bed, she picked out heels that would fit me, she sat me down at the mirror and did my makeup slowly, lipstick and blush and eye shadow, while I watched my own face change. I felt my heart pounding, I felt my cock hardening under the dress, and I felt Lena's hands steadying me, like she knew exactly how much I needed her to stay calm and keep going. She called me beautiful, and she meant it, and I believed her because her hands were gentle and her voice was warm. By the time she zipped the dress up my back, I was shaking, and I was wet with wanting her, and I could not stop looking at myself in the mirror.

Dressed, In Her Mirror

Lena stood behind me in the mirror, her hands on my waist, and she kissed my neck and told me to turn around slowly so she could see all of me. I turned, I let the skirt swirl around my legs, and I felt the heels make my legs look long and the dress make my waist look small. She ran her hands over my hips, she touched my breasts through the fabric, and she whispered that I looked gorgeous, and I pressed back against her, hard, because being dressed and desired at the same time was the hottest thing I had ever felt. I wanted her to take me, dressed, exactly like this.

She led me to our bed and laid me back on the sheets, still in the dress, still in the heels, and she kissed me hard and then kissed down my chest, my stomach, and my thighs. She lifted my skirt, she found my cock already hard under my panties, and she took me in her mouth, slow and wet, while I arched and moaned and gripped the sheets. I came in her mouth with a cry, still dressed, still beautiful, and she swallowed and looked up at me and smiled, and I had never felt so wanted in my life.

Beautiful, And Then In Bed

Lena was not finished with me, and I was not finished with her. She stripped off her own clothes, she climbed on top of me, and she rode me slowly, her dress still around my waist, her heels still on, her lipstick smeared from kissing me. I held her hips, I thrust up to meet her, and I watched her face as she took me deep, moaning, telling me I was beautiful, telling me she loved me dressed like this. I came again inside her, shaking, with her hands on my chest and her mouth on my neck, and I held her there until we were both breathless.

Still Dressed, Still Wanting Her

After that, we lay together on our bed, and I was still dressed, still hard, still wanting Lena again. I did not want to take the dress off and pretend the night had not happened. I wanted her to keep me dressed, I wanted her to fuck me again in the dress, and I told her so, and she laughed and rolled me over and took me from behind, lifting my skirt, holding my hips, thrusting slow and deep until I was moaning into the pillow and coming for the third time that night, with my heels still on and my makeup smeared.

We showered together after, and she helped me out of the dress carefully, and she kissed me, dressed and undressed, like both versions of me were hers. I kept the dress out after that night, not hidden in a drawer anymore, because Lena had dared me to be seen, and I had loved every second of it. That night was not a joke, and it was not a secret anymore. It was about being dressed, being beautiful, and being desired completely by the woman I love.