This is a print version of story My first time with another crossdresser. by sissypantyhoseboy90 from

My first time with another crossdresser.

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my b*****r and s****r. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer to waist with reinf***ed toe suntan wolford pantyhose. They were incredibly silky and soft. i rubbed them on my face and then i smelled them, and then became hooked. the smell of her sweaty feet and silky hose made me want to wear them, so i did. and being 5 years old i was very small, wen i put them on, the waistline was at my neck, but didnt care, the feeling of being wrapped in silk drove me crazy. So since i was 5 years old ive been wearing pantyhose. id say wen i was about 10 i started masturbating. and in the last story was my first time being with a woman wile crossdressed. now this story is about my first time with another crossdresser at the age of 18.

it was a friday night, just got out of school (senior year), and my buddy james and i were talkin in the hall by my locker. james says to me " we should git some beer and git a bonfire goin tonite, get some honeys over and git shitfaced!" I was like "yeah im down. Ill talk to johnny and Brandon and git some more poeple to come." we parted and i went out to my truck and got on the phone with johnny, set up a time and place and he called all the boys and girls to come tonight. well i called a friend of mine, ken, to come to the party tonight, he was a senior and full blow gay, and everyone picked on him, but i wanted him to come and have a good time. he agreed, and i went home and packed my truck full of fire wood and a cooler full of stuff for cookin. got my b*****r to git us some beer, 4 30packs of coors light and a couple bottles of whiskey and tequilla. I picked up john and brandon and we drove back in the woods to our party spot, set up the fire pit, filled the coolers with ice and beer, and everyone started showin up around 7pm. my truck was blasting country music, were all gittin d***k, havin a good time, and here come walkin down the trail, ken. I was relieved to see he showed up. cause like i said, good k**, but not alota people accept him, but i do. i tossed him a beer and said join the fun man. i had grils on both my arms, im shootin shots of tequila and poundin beers, and im fuckin d***k. Its now midnight and people are startin to pass out and what not, and i see ken sittin on a stump, lokkin kinda down. i stumble over to him, "ken, whats up?" he said " everyone kinda ignored me tonight but the girls." and i was like, " well man, i dont know what to tell you, but u gotta loosen up and be more easy going instead of all uptight n shit." i sat down on the log beside him, " dude its cool u showed up tho, cuz i never see u around." he said " well its cuz i like to be at home doing stuff." i said " doing what?" he said " dressing up like a girl." it kinda freaked me out to hear someone else with a womens clothes fetish. I thought he was just a gay. I said "really? Show me." he looked puzzled and i pointed to my truck and we got in and drove to his house. we went into his basement where he basically lived and opened his closet. FULL of womens clothes, and i started to git hard. H said, go wait over there. so i sat on his bed wile he went in the closet and changed. He came out wearing high heels, black thigh highs, a thong, a pink corset, a wig and lipstick. I was so hard at this point, i said " ken" he cut me off "its kaitlin now", "ok, kaitlin, i had no idea how, sexy you are!" she smiled at me and walked over to me, layed me on the bed, and started kissing me. she layed right ontop of me sliding her tongue in my mouth, i could feel her boner against mine. i stopped kissing her for a second and said " would it be hot if u dressed me up too?" she replied " you want to?" i said " i sure do!" she selected a pair of stockings with straps, a thong, and a lace bra for me, also gave me a wig and lipstick. I dressed and we immediately returned to making out, i wrapped my stockinged legs around her pulling her close to me while massaging her tongue with mine. i toook her cock out of her thong and started jerking her. she started to moan. i rolled on top of her and i went down on her hard cock, sucking her hard and i bobbed my head up and down her shaft. i gently squeezed her balls as i sucked her. she pushed me off of her and she turned, and stuck her ass in my face, and got us into a 69. her mouth felt so damn good on my cock, i couldnt help but agressively suck her cock, i could have blown my load in her mouth but i wanted more of kaitlin. so i pushed her off of me and i told her to git on her knees and i slowley etered her ass with my cock, she was moaning quite loudly and i pressed deep into her, her ass was so tight and felt so good, i shoved my entire cock inside her. pumping away in and out of her, both of us moaning in pleasure, i told her to lay on her back and i picked her legs up on my shoulders, and i fucked her deep and hard, i pushed all in and leaned in for a kiss and went back to fucking her, i stuck her sexy little toes in my mouth and just from that, i blew a hot load of cum right in her ass, i pulled out and she looked at me and told me to lay on my back and she penetrated my ass, her cock felt so good going inside of me, hurt at first but i didnt care, i was so horny. she thrusted away in and out of me. it didnt take long for her to blow her load in me wich felt so fucking good! we layed next to eachother, cum oozing out of our asses and i said "kaitlin, this has to stay between us for a while, till i come outa the closet" she agreed and to this day, i still visit kaitlin. oh and by the way, my girl name, which id like to be known as, is Krystal.

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