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Curiosity in Crossdressing: First time in Panties  

Littlelyte 27M
6 posts
8/29/2019 7:05 pm
Curiosity in Crossdressing: First time in Panties


I’m pretty submissive when it comes to sex. Any demands I may have are usually about my partner being dominant, and taking control of me during sex. I love to relinquish of power for a time, letting my body be out of my possession for whatever use my partner at the time wants. Use my mouth, my hands, my ass. I’m all yours…

I would be lying if I said I never considered crossdressing. It’s been one of those taboo thoughts in my head for a while. The thought of wearing a nice pair of panties, with a matching bra, maybe a low cut tank top and shorts that show off my butt, was a thought that turned me on all the time (writing that started to get me hard already…)

When talking to men online, I started bringing up my curiosities in possibly crossdressing. The first guy that liked the idea was, of course, called daddy. All of my hookups tend to take that alias. He was in his late forties, average built body with not much body hair. Short dark hair, and a good cock on him. He was also “straight”. He didn’t want to kiss, and wasn’t going to mess with my penis in any way, which I was fine with. I was looking to suck and fuck, and that only needed his cock. But when I told him about wanting to wear women’s clothes, that got his attention.

I was “his little girl” from that point on. We started talking as the daddy/little girl type of talk.
“Are you going to be a good girl for me, baby?”
“Yes daddy.”
“You going to choke on my cock, baby?”
“Oh, yes daddy! I’m already thinking about your hard cock in my mouth…”
“Oh baby, you’re gonna be a good girl for daddy, aren’t you?”
“Fuck yeah, daddy!”

We exchanged face pics, which sealed the deal of an online hookup. If you get far enough that I show you my face, we are guaranteed to fuck. So we showed our faces, he gave me his address, and went over. He met me outside his place, standing next to a gate to his backyard. We greeted each other, like one does meeting an online stranger who you’re about to have sex with. He opened the gate, and led me in.

It was a barren backyard, with not much besides random miscellaneous things that didn’t stick to memory. But what did catch my attention was the camper, where daddy was walking towards. He unlocked the door.

“I have someone staying over in my house, so we are going to be in the camper, so we don’t disturb them.”

This probably should have been a red flag for me. But I was too horny and inexperienced at the time. So I walked right into his camper without any thought about it besides daddy’s cock.

It was pleasantly dark inside, with enough light shining through the closed curtains to distinguish things in the camper, but not in detail. There was a full-sized bed in front of the door, and to the side were cabinets. On the counter was a dildo--larger than anything I’ve ever had in my ass--and a bottle of lube. Daddy closed the door behind me, and started rubbing my ass firmly. I felt myself getting hard by his touch. He slapped my ass hard.

“You like that, baby?”
“Fuck, daddy.”
“You going to be a good girl for me?”
“Yes, daddy. I’m your good little girl.”

He reached to the counter, grabbing something I didn’t notice was laying next to the dildo. It was a pair of panties. They were plain black, and aren’t the type of panties you picture when you think of sexy. But they were still panties. When I got home, and was able to look at them in a better light, I noticed the dried cum stains on the front. I guessed they may be the panties for the person he doesn’t want to disturb in his house, which I feel guilty saying that turns me on with the thought.

I was already unbuttoning my shorts before daddy told me to strip. I didn’t put on a show since that’s not what he wanted. I was about to give him what I wanted. Because I was his good little girl. His overly horny little girl, that was already dripping precum by the time I was sliding my panties on. He gave me another hard slap on my ass.

“Oh fuck daddy. I want you so bad.”
“Good girl,” --he started rubbing my ass, firmly grabbing a handful, then slapping me again-- “Show me how good of a girl you are, baby.”

He guided me down to my knees, and I excitedly pulled down his shorts to show his standing cock. I gave him a kiss on the tip, feeling a drop of precum spread on my mouth. I moved my tongue around his cock, wrapping around the head, and sliding down his throbbing shaft. I took him in my mouth so deep I started choking. I got too excited, but I don’t care. I moved up and down, up and down, gagging and spitting on his hard cock, thinking about nothing else besides his cock. He grabbed my hair, moaning with pleasure. I was a good girl.

He pushed me to the bed, face down. I raised my ass up for him, giving him what he wants. What I want. I felt his lubed up fingers rub my tight ass hole. The lube was cold, but pleasurable. I knew what it meant. He slid his finger inside me, slowly, moving his fingers up and down inside me. I moaned for him. “Oh daddy. Yes daddy. Fuck!” I looked down, seeing my hanging cock dripping from excitement, and daddy sliding two fingers inside me. He stretched me out, moving his fingers apart inside me, filling me up. I moaned louder and louder for him. I hoped I was good enough girl for him.

He pulled his fingers out of my well-lubed asshole. I turned to lay on my back to watch as he went for the dildo and bottle of lube.

“Good girls love to fuck themselves with big cocks. Show me how much of a good girl you are, baby.”

I nodded. I couldn’t respond verbally. I was in another place after being finger fucked like that, and was already missing having my ass filled. He gave me the dildo. Luckily he lubed it for me, because I was putting it in my ass right away. Working the head of it in was not easy. Even with being stretched out, this was the biggest cock I’ve ever taken. The pressure from the stretch was something I can’t explain in words. Think of the best feeling in the world, and that wouldn’t compare to this. The more I pushed the dildo in, the more I felt stretched, filled, the most extreme, pleasurable pressure I’ve ever felt. My cock throbbed, but I didn’t touch it. Daddy didn’t want that. He wanted to see how deep I can put this dildo in my ass. And I was gonna show him.

In. Out. In. Out. In and out I thrusted the massive dildo inside me. Fucking my mind empty, thinking only about daddy and this massive dildo in my ass. It was all I needed. I came so hard, first time without touching my penis. The load shot onto my chest and stomach as I kept fucking my ass.
“Fuck baby! You’re a really good girl.”
Daddy grabbed my hand holding the dildo in my ass. He pulled out the dildo, throwing it on the bed, and immediately ramming his hard cock into my gape hole. He fucked me hard and fast. I felt like I was still coming, excited from feeling a real, throbbing cock in my ass. He didn’t slow, he only went hard, balls pounding against my ass. It didn’t take him long to cum inside me, shooting his hot load deep inside me.

He pulled out after thrusting out the last of his load. I felt some of it drip out of my used ass. The warmth filling up my body. I still had my load covering my torso as I laid there. Daddy gave me a towel, but I was still not back from where one goes in moments before, and during orgasm. I was high from him. I wanted him to fuck me again, but he had things he needed to do, and I had to leave.

That was one of the first time I wore panties for anyone. And the start of a curious<b> fetish </font></b>of mine...

HAMONMAN 64M
13128 posts
8/29/2019 11:12 pm


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