It Started As A Joke

It started with a joke, just being ridiculous to get a laugh.

It was an otherwise normal day. My work has a "use it or lose it" policy on vacation days, so here I was at the end of the year with a few days to spend, so I had time to kill and was watching yet another unsatisfying horror movie while the wife worked from home in her office. After lunch, as she was going back to her meetings, I told her I was going to do the dishes, then go try on her sexy underthings. Like I said, just making a joke, as it wasn't a kink on our collective radar at all. She rolled her eyes, gave me a snarky 'whatever' and we went on with the day. I didn't go through with it, the joke had done what it was intended to do.

But...

As she went to work and I finished my movie, the thought kept poking back up in my mind. Maybe I should go take a look and see if anything looks like it would feel nice?

Maybe just some panties, she does have a lot that I like her in, maybe I could look sexy, too?

Maybe she'd think it was hot to see me dolled up, and role play a girl-on-girl scene?

I pushed the thoughts aside for a couple days and enjoyed the downtime from work. Then she had a slow day and was working from the couch and hanging out more than anything. We had been talking about plans for the holidays and stuff we wanted to get done around the house before I went back to work, and I said there was one more thing I hadn't gotten to yet.

"What's that?"

"I never did go up and try on your lingerie the other day."

She rolled her eyes again. "If you want to, you know where it is. I've got some work to do for a bit. Have fun." She turned back to her laptop and started typing. I took a big breath and started up the steps to our room, heart pounding. Was this really going down? Was I sure about this? I closed the bedroom door and took a minute to consider, then began looking through her stuff.

Here we pause to note, I'm not a feminine guy, and this was something way outside our wheelhouse. I'm about 5'11", total dad bod. She's 5'1" in heels and what the enthusiasts call thick, with long red hair and a fantastic ass and tits. Her things may not fit well, but I guess we were going to find out.

I found a pair of fishnet tights and a faux-leather dress that looked promising and began to strip down. To my frustration, I found fishnets don't go on as easily as they come off. I sat on the chair in the corner and struggled for a minute to get them on without ripping them. It felt good, dirty and sexy and taboo. I stood up and tried to slip the dress on. It was tight on my belly and wasn't really working for me. I was about to pull it off and give the whole thing a miss when I heard the door start to open. She walked in, kissed me and asked how it felt. I stammered through an answer that tried to convey how odd and simultaneously hot it was for me. She looked me over, said 'Try this dress, it'll fit better,' and pulled out a little black thing with straps on the back. I slipped into it, and felt like a sexy, slutty thing. I stood in front of the mirror a minute, admiring myself, and slid the dress up a little to see my growing cock wrapped in fishnets. She gave me a stroke or two, and grabbed a necklace from her nightstand. She draped it around my neck, murmuring, 'my pretty boy, let's have some fun.' Taking my hand she led me to the bed and we laid down. She ran her hands over my thighs, the tights adding new dimensions to the sensation. I was now leaking precum like a fountain, running down my length and soaking through the stockings.

"I guess you're enjoying this, huh? My pretty man all dressed up for me... Let me get on top of you and ride my pretty man til he cums." She put action to her words and stripped down, then pulled at the fishnets until they tore a bit and released my cock, still running like a tap with precum. She gave it a lick and sat up with a mischievous look. She reached for the nightstand drawer where we kept our toys and things.

"Do you need a cock to suck while I ride you?" She produced one of her dildos and held it to my mouth. We were definitely off the map at this point, but I was game. I let her slip it in my mouth and gave it a couple licks and sucked on it as she lined me up and settled herself onto me. She took control and rode me, while fucking my mouth. 'Don't cum yet, baby, let me ride my pretty man's hard cock a while.' Of course, saying don't cum yet is the fastest way to make a guy cum, and I was already in a state, so it wasn't long until I exploded in her wet pussy. She rolled off, my cum pouring back out of her in a flood, and I grabbed her magic wand. I handed it over and slid a finger or two inside her as she finished herself, playing with the cum and wetness as she bucked her hips and gasped for air.

Spent, we laid there a few minutes and caught our breath. She sat up, said 'I need to get back to work. You need to handwash that cum off those things or you'll need to buy me new stuff. In fact, if this is going to be a thing, you should buy your own, too.' Guess I'm going shopping soon...