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My first time with a man

"My first time with a man"

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I am a straight guy, but I have always enjoyed dressing up in skirts, hose, panties, painted toenails and heels. I had only ever dressed at home for an occasional cam session. I really loved getting dressed up for men, but never dared to do it in real life.

One day I was really horny and feeling very daring, so I answered an ad on a local app from a guy looking for a 'panty wearer".  I figured, what the hell, so I send him a response.

I'm not 100% passable, but I look OK fully dressed. The guy answered me back pretty quickly.  He seemed very nice and not too pushy, so I agreed to invite him over to my place.

I was fully dressed, freshly shaved and was feeling very girly. I was also extremely nervous and ready to back out, but the horny part of me said to go for it.  He arrived at my place looking very handsome and even better, he brought us a bottle of wine. I invited him in and gave him a very awkward hug and poured us both a very needed glass of wine.

I was wearing a short black skirt with no hose, black patent leather pumps, fake boobs, the works. He mentioned that he loved the loved the look of bare skin in high heels, so I did to make my man happy!

I was still extremely nervous to the point to where my hands were shaking, but I was also so turned on by the fact that I was finally dressed up in a room with a person, not just a computer screen. 

We finished our bottle of wine, talked a lot about our likes and dislikes and we got closer to each other and started kissing. My heart was pounding, my panties were full of pre-cum and I was loving it.

I went ahead and started working my way down to his cock, kissing his neck, unbuttoning his shirt and finally his pants. I had never been with a guy, so this was going to be the first cock that I would have in my mouth.

I took his cock out of his pants and he was already fully erect, large and shaved. I went ahead and licked his balls and underneath his shaft. I began licking his pre-cum off his impressive head and putting him in my mouth.  I loved the salty taste of it.  I started working him in my mouth and down my throat, gagging a bit, but I eventually I got the hang of it and had him fully in my throat, coming up for air when I had to.

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I was loving having his cock in my mouth and while sucking him I was wondering why I had waited this long to try it.  After a while I could feel him tensing up and he told me he was going to cum.  I though about having him cum on my face, but I really wanted to taste him since I love the taste of his pre-cum. He began cumming in my mouth and throat and I was so turned on that I swallowed every drop.

We took a break, and opened another bottle of wine. We had a few more glasses and he told he that he really wanted to fuck me, but that he wanted to play with my body first.

He lifted up my skirt, started licking my thighs and he took off my heels. He began sucking my red painted toes which really turned me on.  I didn't how much of a turn on that this would be. He pulled down my panties and licked all around my butt and my hairless cock. I was about to explode and couldn't wait to have him in me. He rimmed me and lubed me up, preparing me for him.

Finally he started sticking his head in me slowly.  It hurt at first, but he was so gentle that I found myself pushing myself against him because I wanted more. He continued entering me until he was fully in me. It felt SO good.

We started off in the doggy position, but then he stopped and laid me on my back. He raised my legs up to his shoulders and stuck it in me again.

I loved this position so much better than the doggy position. I could feel his cock in me so much more. He then began sucking my toes again as he continued fucking me faster and faster. He told me that he was ready to cum, so he rammed his cock in me even harder till he was finished cumming inside me.

I loved every minute of it and I had never felt more feminine in my life.  After that we kissed and agreed to meet up again.  I can't wait!

Published 
Written by akcass2002
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