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One of My First Experiences Dressing for Someone Else (All True)
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This happened a little while ago and I'm dying to meet with this guy again:

So there was this guy I had met with once before. He was a pretty decent guy and was very into the dom/sub dynamic. Which I’m totally into. So I go over. He has tons of female clothes laid out over his bed. Spandex, lingerie, costumes, etc. I grab a few and go to the bathroom. I try the first on come out. Then I try on I think two more and he tells me which one is his favorite. His favorite was a Snow White outfit with red panties and red tights. I also had a blonde wig and some red lipstick on. He had told me online that when I came out dressed he wanted me to present myself for inspection which he showed me a link to. Basically I came out and put my hands behind my head, legs wide, eyes ahead. Anyways. He had a little tool, like a leather paddle but it was more like a flyswatter (sorry I don't know what it's called). It was Pretty soft. But he used it to reposition me and show me how to properly stand in the position for him. Then he gave my clit a little smack. He took my hands behind my back and handcuffed me. (It was Velcro cuffs so even though we had a safe word I felt safe I could get out if things weren’t comfortable or I didn’t feel safe). He showed me a number of toys he had and said he wanted to try this new one he had gotten. It was a vibrating butt plug. He pulled down my leggings and panties. He told me to bend over his bed and lubed me up. He then inserted the plug in me and pulled back up my panties and leggings. It wasn’t too big but I was very aware of it. Then he turned it on. (It had a remote)
So my ass starts vibrating and I’ve never had any vibrations in my ass before but it actually felt really good. There were a couple of settings he flipped through and he watched my reaction to each. He smacked me a few more times with his swatter and told me what a sissy I looked like and asked if I like that. I told him yes sir I did (as we agreed I would only respond to him as sir). He told me that was good and to bend over the bed again. He turns the vibe way up and by this point I’m moaning because it’s hitting me right. He smacks my ass a few times. Next thing I know I was starting to hump the bed.
I didn’t even notice at first but he pointed it out. He said look at you sissy you’re trying to rub your clit. (Because my hands were handcuffed I couldn’t touch it). He said scoot farther on the bed and hump the pillow like a girl. So I scooted up as he positioned the pillow and did as I was told. It really felt great. He told me to keep moaning and say it felt good on my clitty so I did.
After a bit of this he shut the vibe off and told me to stand up. He felt my clit through my panties and leggings with his swatter and could tell I was aroused. Next he got out his big vibrator. One that has a big round head. He turned it on and placed it right on my clit. He asked how I liked it I told him I really like it sir. He moved it up and down, vibing my head and shaft. It was such a unique experience. I could tell he really liked watching my reactions. He did that for a while. He told me he was going to vibe me for a long time and not let me cum. Well, after I while I told him sir I’m going to cum I can’t help it. It was too late and next think I knew I was cumming in my panties and leggings as he continued to vibe me. He told me I was a very bad girl for not listening. I had a big puddle that was very visible and my cum started dripping up the ground. He vibed me a little while longer for his enjoyment even though it was pretty sensitive on my clit now.
He took my hands and put them on a nail he had in his wall that was over my head. He then had me dance/ flail as though I was tied up (which I was) as he pulled down his pants and masturbated.. He came on the floor and then untied me and we all got cleaned up.

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4 years ago