My First Time With Another Crossdresser. free porn video

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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 brother and sister. 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 reinforced 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 brother 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 drunk, 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 drunk. 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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Note: This is not your usual Lush story. It is an experimental play in a theater of the absurd style. There is no sex but it is an entertaining comment on marriage. I encourage you to indulge in something different. I think it will make you laugh and maybe cry. Scene: A formal living room. Mortimer is seated on a sofa in the center of the room when Myrtle enters and sits on the sofa next to him. She is wearing a blue floral dress and a pearl necklace, her gray hair is tied in a bun. Mortimer is...

Lunchtime Munchtime

As was his habit at lunchtime, Hal left the building and walked through the office park for exercise. It was a partly cloudy day, and for the moment it seemed overcast. On his way to a small path through the woods, he saw her. Sandy was an attractive redhead with a sensual voice who almost always wore a tailored blouse, a roomy ankle-length skirt, and one-inch pumps. Her wardrobe varied in color, patterns, and material, depending upon the season, but always the same ensemble. Hal watched as...

Wartime

Elizabeth Fleming told me some of this story in the years before she died, aged eighty, in 2010. The more graphic scenes are mine but the emotions and surrounding history are hers. She was my Great Aunt, great in so many ways for she was the third family member I ever revealed my sexuality to, the first two being my parents. I had known since girlhood that she shared a cottage in Hampshire with her friend, Portia, but had never known their relationship was more than sisterly. When I told her...

Lesbian

FaceTime with Ann Next Door

I never FaceTime. I'm not a adolescent girl. I don't need to see your face when a simple text will do. Call me an old bastard, get-off-my-lawn type, but that's the way it is. (By the way, I'm not that old).So when that mechanical beeping emanates from my phone that someone wants to FaceTime me, it's definitely out of the ordinary. Especially when it's 10:30 on a Tuesday night. I got to my phone and it said "Ann FaceTime video."Well, this was different. Ann Next Door and I been fooling around on...

A return to Js nanother true story

Here I am back at “J’s” the Guy that took my anal virginity.I have used his bathroom and ensured I am squeaky clean were it matters.Today he already has a friend staying with him so I know I will be busy. ”S” is his name and I know they have been friends and fuck partners for many years so they know what they want and how to get it.It starts the second I enter the bedroom I am encouraged to get on my knees and I am presented with two cocks to suck on. I opt for “J’s” as it is almost 10” long...

Daytime friends nightime lovers

She wanted to remember. The hookah was a beautiful piece. It stood at 4 ½ feet. Dark red… it always was her favorite color. This hookah was her personal prize. It only had one hose, one smoker. She pulled the airtight box from its hiding place and opened the lid. Once released, the heady aroma drifted, tickling her nose. The new batch of bud was a dark green, but the crystals were so thick it turned everything pastel. Breaking it apart just enough to smoke easy, she arranged the weed in...

Daytime friends nightime lovers

Introduction: While a few details have been tweaked, this story is as close as I can remember it Prologue She wanted to remember. The hookah was a beautiful piece. It stood at 4 ½, feet. Dark red&hellip, it always was her favorite color. This hookah was her personal prize. It only had one hose, one smoker. She pulled the airtight box from its hiding place and opened the lid. Once released, the heady aroma drifted, tickling her nose. The new batch of bud was a dark green, but the...

Sandy and RandyChapter 2 Daytime Funtime

After the close call and excitement, in more ways than one, of that first night together, Sandy decided they better cool it a bit so Mom wouldn’t get suspicious. Mom also went back on day shift, 8am – 8pm, so bedtime was less private, but days were not such a problem. Randy tried to act normal around Mom and of course, around Sandy, but he did have some issues like being quieter and more protective. Mom just thought he was getting older and closer to starting into puberty, especially now...

Another Springtime Ch 05

Chapter 5: Encounters On The Open Road Looking back now afterward I still cannot make sense out of what happened that day at the motel at LeGrande, Oregon. They had picked up our trail somehow, although I think it must have been a matter of pure chance. I have reviewed it now a thousand times and cannot see where we left a trail to open ourselves to their tracing. Nevertheless, we had an encounter on a Tuesday morning after a pleasant stay in LeGrande and breakfast at the restaurant across the...

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