My First Crossdresser

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My First Encounter with a Hot, Sexy Crossdresser.
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Only a few years back in my young 20's I discovered Craigslist. I had no idea something like that existed and was immediately drawn to it. After building up the courage to meet with a few different guys, I found an ad in the T4M section on their website. A gorgeous cross-dresser with long legs and a stunning body.

I got instantly hard when I see this girl's pictures. A slim sexy girl with an ass to die for and a desire for cock. After some back and forth emailing for a few days we agreed to meet in her place. I went around to her place late that night when the coast was clear of her housemates, about 1a.m or so. My heart was pounding and I was really excited. It felt like what I was doing was sneaky, wrong and naughty and I loved it.

I parked my car around the corner as not to raise suspicion. I then called her from my phone with my number set to anonymous. She answered with this gorgeous feminine voice and told me to come in. I walked into her garden, walked over her decking and knocked on her window.

She lived on the side part of a house, with nobody above her. I got to her window and I knocked. After a few moments, as I stood in this random persons garden hoping I wouldn't get spotted, I heard the door unlock and she slid the door open. She disguised herself behind the curtain and then I slowly and nervously entered, into a pitch black room.

Now it was dark enough to the point where we wouldn't make out who each other was or blow either party's identity, but there was enough light where we could see each others body and silhouette. She had long dark hair, wearing super sexy high stocking's with a g-string, a corset and 6inch high heels, which made her ass so perky and desirable.

I stood in the middle of the room and she very slowly and sensually walked over to me. I felt such a rush, my heart was racing and my cock was rock hard. Just as we were nearly face to face she slowly turned around, put her hands up in her hair, stuck out her ass and pressed it against my Cock and started grinding on me.

She turned around and then lifted up her hand and gently placed it onto my cock over my bottoms. She could feel how hard I was and she loved it, letting out a little moan, knowing she was about to devour my Cock down her throat. She began slowly rubbing me, building up the excitement. She then took my Cock out of my pants and started to stroke it, back and forth with her hand. I was so fucking horny at this point and I wanted more.

Without hesitation she got on her knees ready to take me into her wet, warm mouth. I wanted my Cock in her mouth more than anything. What felt like an eternity she began to move her head forward, mouth open ready and willing for my hard Dick.

She wrapped her lips around my shaft as she slid me into her mouth. Mmmmmm, it felt soooooo good. She had the hottest mouth my cock had ever been in. She slowly sucked my cock, back and forth, slowly and sensually. After a few minutes of bliss she really got into it.

She started going faster and faster and then. she took my WHOLE COCK into her mouth and down her throat. OMG. it felt amazing. Hearing her gagging on the length of my Dick and the slurring and moaning noises she would make turned me on even more. After a couple of minutes of her Deep-throating me, I pulled out of her throat, as i was about to Cum and I wanted more, I didn't want to Cum yet, it was too Good. She was ready and wanting to be fucked at this point, as she really worked herself up as she took me deep down her throat.

I wasn't finished with her mouth yet however. I made her lie on her bed, on her back with her facing the ceiling and got her head hanging off the bed with her mouth and throat wide open and ready to be fucked. She was reaching out for my cock, trying to devour it but instead I stood over her, my legs either side of her face and I lowered my Balls into her mouth. She sucked them and lathered my balls with her wet, pre-cum filled tongue.

After I was satisfied I lifted my balls up and out of her mouth and began to feed her my cock. She couldn't get enough of my yummy hard dick, so I rewarded her by fucking her throat. In and out, getting harder and faster. She loved it and I loved hearing her gagging on me!. I then stuffed all of my cock down her throat and made her lick my balls as my dick was in her throat, and she did.

I was ready now, to fuck her sweet, sexy ass and she wanted it so bad too. I stood her up, bent her over the bed and began to worship her ass. I caressed each cheek in the palms of my hands as I began to feel her entire body. I ran my hands all the way down each leg, wrapped them around her inner thigh, stroked the outside of her panties, felt her tits, hips, waist, everywhere. I needed to eat her ass now. I then removed her G-string which gave me access to her sweet asshole.

I spread her ass apart and from above spat down above her crack. The spit slowly dripped down between her ass, over her asshole and onto the floor. She moaned as she felt the spit trickle down between her cheeks. On my knees, I then began to lick up and down between her ass and asshole. She loved it and began to push her ass into my face. I loved having the feeling of being submerged in her ass.

I started to focus on her asshole and get it nice and wet for me to fuck. I lengthened and stiffened my tongue and began to tongue fuck her. I loved it and so did she, pushing herself in and out of me, thrusting back and forward with me tucked into her ass from behind. She began to beg for me to fuck her, she was so turned on and wanting my cock deep in her ass. I obliged.

I made her stand up, walk over to a dresser she had, bend over and lean on it. She still had her whole outfit on, apart from her panties which I removed earlier. With her long stocking covered legs and high heels, she stuck out her ass, inviting me to enter her. It was the most desirable Sight i had ever seen.

I approached her from behind, grabbed her by the hips and spat on her ass. I then began rubbing the head of my dick over her wet asshole and slide right into her. I slowly pushed my hard cock all the way down and into her ass. She yelped in pleasure as her head tilted back and her ass tightened. She loved it and couldn't help moaning.

I slowly fucked her, in and out for about 5 minutes. At this point I noticed she had a tramp stamp which turned me on even more, so I began to fuck her harder and faster, like the good little slut she was. She loved it and so did I. She began to fuck me with her ass in sync with me fucking her from behind. We fucked and fucked and it was amazing.

I was about to cum, but managed to pull out. She then lay on the bed, face down, ass up(her favorite position). I mounted her from behind and fucked her into Orgasm. I fucked her nice and deep. I knew i wouldn't be able to hold off cumming for much longer, so I had her get on top of me as I lay on the bed and ride my dick. She rode me facing me and I Slapped her ass, her moaning with every slap. On the brink of cumming into her ass I made her dismount, turn around and fuck me, with her ass facing me.

I sat on the edge of the bed with my arms supporting me and sitting up. She lowered her tight little ass between my Legs and fucked my dick more. She was riding me so good, up and down and side to side, it felt incredible. I was getting so close now that I had to cum. I tried my best to prolong it, but it was too hot. Just as I was about to cum,

I said, "Fuck I'm going to cum."

Without me asking she then dismounts my cock, gets on her knees and devours me. She wants my cum like it's the last drink on earth. She sucks me so good and fast that I can feel the cum building in my balls, about to explode. After a few seconds I let go and I start shooting cum down her throat. She is moaning along with me, as she swallows every single pump of my hot cum, not spilling a drop.

I got dressed and left through her sliding door, only to come back for more!.

If you liked this story please comment, if it turned you on, made you touch yourself, stroke or rub yourself or made you cum, let me know too!.

Also leave comment if anybody would like to hear more of my sexual encounters!!

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AnonymousAnonymous11 months ago

Don't forget bring all your friends need cock

AnonymousAnonymous11 months ago

Iam that cross dressing whore you and your friends should come over and gang bang me I suck fuck my mouth and ass I will swallow all of yout cum and love dp in ass and mouth tied up and fucked yours truly cum slut whore iam waiting for cum please I crave it

AnonymousAnonymousalmost 4 years ago
No mention

How the low hanging fruit she had between her legs ?

AnonymousAnonymousover 7 years ago

Could you do your Second one.. You are very descriptive and I love the story

AntoinetteBelleAntoinetteBelleover 7 years ago
Hot.

Very hot James. I see lots of comments from guys here, but many of us gurls desire a hot, quick encounter like you described too.

Xxxxx

Antoinette

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