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My First Crossdresser

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 up with a few guys a couple times i found an add in the T4M section. I got instantly hard when i seen this girls 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 around the corner as not to raise suspicion, call her then went into her garden, walked over her decking and knocked on her window. She lived on the side part of house with nobody above her. A few seconds after i knocked on the window 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 i then slowly and nervously entered into a pitch black room.
Now it was dark enough to the point we wouldn’t make out who each other was or blow either party’s identity but enough light where we could see each others body and silhouette.
She had long dark hair, was 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, it turned me on more hearing her gagging on the length of my Dick and the slurring and moaning noises she would make. After a couple of minutes of her Deepthroating 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 Cock 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 my Cock down her throat and made her licks 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 bad. 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 and bend over and lean on the dresser, 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 some more and by rubbing the Head of my Dick over her Wet Asshole it allowed me to slide right in. I slowly pushed my ready 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. I noticed she had a tramp stamp which turned me on even more, so i began to fuck her harder and faster. 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 and managed to pull out and 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 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 and turn around and Fuck me with her Ass facing me. I sat on the edge of the Bed, my arms supporting me sitting up and she put 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 Soooo Good, i was getting so close now 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 about to Cum”, without me asking she then Dismounts my Cock, gets on her Knees and Devours me. She wants my Cum like its the last Drink on Earth. She Sucks me so good and Fast 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 and 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 and you made yourself Cum from it or even just played with yourself let me know too!.

Updated: October 21, 2016 — 1:30 pm

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