For a while now I’ve been off and on trying crossdressing. Always kept it a secret and never discussed with my wife. I’ve admitted to some bicurious urges and enjoying receiving ass play, but left it at that.
So a couple weeks ago I had some unplanned time off work and was just hanging out while she works from home. One afternoon, going out for a smoke, said to her I was bored and horny so once I smoke I’m going upstairs to try on some of your underthings and jerk off. She rolled her eyes and laughed, other things (not sexy) came up to do that day and that was it. She took it as a joke and we moved along.
Next afternoon, she asked what I had planned and I said I never got done what I was going to do yesterday, maybe I’ll try to do it after lunch. What’s that, she asked. Dressing up in your sexy underwear, I said. She stared for a second and said, seriously? If you want to, you know where I keep them, and went to her office.
I headed up to our room and began to look through things, heart pounding. Was I really doing this? Finally, I figured nothing ventured, nothing gained and began to rifle through her stuff. I pulled out some fishnet tights and a little black dress and began to strip down. As I was pulling the tights up, the door opened and she came in with a look of curiosity and amusement while I awkwardly worked the tights up my legs. She said, are you into this? I told her it was something I’d been low key curious about and seemed like a good day to try it.
I struggled with the dress, and she reached into her stash and grabbed a different one, saying this will fit better. It had ties on the back that she did for me, than took off the chunky black necklace she had on and put it around my neck. I posed for a second in front of the mirror, feeling a little silly but also aroused. I asked her if she was up for her first girl on girl experience, she laughed and said, I want to ride my pretty man.
I laid down on the bed and she took over. She rubbed my cock through the tights til I was leaking precum like a fountain and got her clothes off. Then she ripped the tights open and locked me up and down, while saying I was her sexy, pretty man and she couldn’t wait to ride me in my sexy dress. Then, she really surprised me. She opened the nightstand and took out one of our dildos. She said, do you want to suck a cock for me while I ride you? Then she held it up to my face and guided it into my mouth, fucking my throat as she slid my dick into her soaking wet pussy. I’ll admit, I didn’t last long at all, and exploded inside her in short order.
We laid there a few minutes, and as she slid off, leaving a pool of cum and her wetness all over the clothes, she reminded me that they were hand wash only, so don’t let them stain or they’d have to be replaced. I’ve been nervous about bringing it up again, but also really excited. She did say she’d thought about taking pictures, but decided to save it for next time…