Incidents In A Cross Dressers Life. Part Two (A Tr free porn video

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My first "outing" was with a female fuck buddy. She loved sex. Any time, place, or person. Damn she was a great fuck buddy! She asked about any fantasies I had. I mentioned I always wanted to cross dress in pantyhose, panties, bra, and a great wig. We spent the afternoon shopping and found all of my needs and a great wig that matched my natural hair color. There is a nice pic of me labeled "first pic." in the gallery.

My nipples and cock were rock hard the whole time, especially while she dressed me. While assisting me with the pantyhose (I pretended I never tried on a pair), my boner was front and center. I was so hard that I would punch holes in a one inch piece of plywood. She of course, kept popping it in and out of her warm lips driving me crazy. I wanted to cum on her face SO bad that it hurt. The tight feel of the nylon was delirious. The tight bra pushed my man boobs together and high so it looked like I had lovely B cups. I was surprised that my nipples did not chew their way out of the cups. The wig was next! Once on, she combed it out which sent my asshole into spasms. When she did my face, I was trembling. The lipstick!

The red lipstick did not stay in place long. She pushed me on my back and pinned my body down. She ****d my mouth with her talented tongue. Her pelvis was grinding into my nylon entombed cock, forcing my ass tighter into the hotel mattress, and forcing my ass cheeks to fight the nylon fabric holding them together. Her massive and lovely tits were massaging my bra giving me multiple nipple orgasms (YES they do exist!).

She moved down between my legs and started to lick my hardon through the fabric. This was payback for when, on our first encounter, I chewed through her pantyhose to get at her pussy. (A story for another day). She tore a hole in the crotch to get at my asshole. One finger, then two, then three, and I was nearly in a sex induced c***. Fingers in the ass and a tongue on the cock; does it get better that that?! YES!!!

She produced, out of nowhere, a 10" vibrator and up it went!!!! (I always wondered where she kept it?). She hit the power and I was off to the races. My ass slammed up and down as my I blew my load hard! Trapped in the nylon, my cum shot through the weave like a water stream from a garden hose through a screen door. I'm sure I arched my back as I came and then slammed back down (usually arch up from habit from trying to hit my face and mouth with my cum shots). All I wanted was to breathe and enjoy the full body convulsions. NO - she did not stop fucking my ass with the plastic cock! That sent me off again with a whine and whimper.

I was lying on my back with my beautifully coiffed head hanging off the bed, my arms and legs outstretched like I was about to become the center of affection at a bondage party. Just then, our girlfriend walked into our room and stopped dead in her tracks! I was looking at her upside down as she sputtered and stammered in shock. It's not that she had never seen us naked; it was she was surprised to see another woman and realized that it was me!

Just then, my fuck buddy, rolled me over, pulled me onto my knees and started to piston the vibrator in and out of my sore hole. This was the first time someone else was shoving something up my ass. I wanted MORE! I started to rock back and forth. She reached up and pulled my hair back forcing me to look upward. My eyes rolled back, my mouth opened (I would have been the perfect time for a hard cock to have been forced into my waiting and open suck hole), and I was close to seeing God! She let go my hair and my head slumped down as my ass arched up. I felt her hand sliding up and down over my engorged cock as she gave me a lesson in Femdom.

I came so hard a catapulted off the firmly held dildo, shooting off the bed head first onto the floor. I rolled over (very slowly) and looked up at our girlfriend who, still in shock, was looking down at me. I was panting hard and shaking from the ass fucking. As I was looking up, wondering if I would ever have a real flesh cock fucking my brains out, the girlfriend started to rub her nylon clad foot over my face ordering me to lick it. What was a guy to do; dressed up in pantyhose, his hair and make-up all asunder, fucked out like the slut I am, with a throbbing asshole to do?

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I had dressed up since I was a teenager but it was only occasionally. Usually, it was just lingerie and it was always for me and just for masturbation. It was about ten years ago that I decided I wanted to go further and start using makeup and breast forms and wigs etcetera.Quite by chance one day, I rang an old friend just for a chat. I found out that he had rented his house out while he was travelling. The person on the other end of the line was a woman, or so I thought. We got talking and I...

Crossdressing
2 years ago
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Cross Dressing Cock Slut Party

Sadly this wonderful story is just a fantasy, but who wants to make something similar a reality!?!The evening had taken a while to arrange, but had finally arrived. All 5 guests turned up within 15 minutes of each other and as they did, I fixed them a quick drink and showed them into the living room to get to know each other. Alan was a suited businessman in his mid thirties. Dave and Brian were dressed casually in jeans and Tshirts and both in their mid forties. Jeff and Keith were my age,...

2 years ago
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Gotham City by Catwoman

[ Update: Free Use World !! The main storyline will continue. Please enjoy using Catwoman's lesbian anal fetish mind control Gotham City. ] Prologue: Batgirl struggled with the nylon ropes binding her in place. They dug deep into her costume across her nips and down the crack of her pert ass. There was little else she could do. The thin ropes bound her thighs and ankles together in kneeling position. Her arms were firmly tied behind her back and those ropes were tied to the ones around her...

Mind Control
2 years ago
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CrossDresser Delight

As a cross dresser you feel like such a woman when you have on your sexy panties and bra, and other feminine unmentionables. Sometimes you just wear them underneath your boy clothes. But sometimes I like when you have a dress and even high heels on too. I get to look at you, a beautiful and sexy woman. You get to tease and titillate a guy like me with your sexy body. You make me so horny and hard when you prance around the house looking so pretty. You always wiggle your sweet ass when you...

4 years ago
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Young secret crossdresser8217s 1st experience

Hello everyone. I am  Anuradha / Sameera, a Secret Crossdresser of 29 years old from Telangana. My breast might be around 34-36 as 36 size too fits well. I love sports bras and padded bras. started in my junior college days when my friend became my boyfriend. It started with him sitting beside me. We used to stroke each other’s cocks secretly under the bench. The handjobs slowly turned into blowjobs. I also had my boobs squeezed by a few others in the class. But I was too scared to tell my...

3 years ago
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Telling Mom Im A Cross Dresser part 18 Missys Halloween Party

I had enjoyed my week of sex with Thomas and Lemar but in the end it left me sore and used but not like I was complaining. It was now getting close to Halloween and mom and I were making plans to go to a Halloween party a few city blocks away from us. Yeah, sounds kind of boring I know but it was no ordinary party with costumes and drinking alone. It was an orgy for bisexual people. It was only a few days away and Mom and I decided to go costume shopping both online and in the local stores to...

4 years ago
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Xena Versus The Spartans

It was a time of horrible raids by terrible marrauding hordes, which caused untold misery, fear and poverty in all of Pelopones. It was a time when Xena and Gabrielle were needed by all the towns, before it is too late, but she was nowhere to be found. The century before had been a good time for all, under the Cooperation Accord of Olympia, there was piece between all the polises, and Xena could concentrate on petty crime and feuding Gods. But now Xena had been on a mission in Asia for years,...

1 year ago
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Robin and the Catwoman

“Oh my head.” Robin whispered as he stirred awake. It took a few moments for him to fully regain consciousness. His last memory was of chasing someone across the Gotham rooftops, now he was in someone’s apartment. “I’ve been captured!” He screamed in his mind as he suddenly realized he was under restraints. Taking a deep breath, he willed himself to think calmly, just as Batman as taught him. Take stock of the situation, then form a plan of action. The room was in semi-darkness, illuminated...

4 years ago
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Lifeboat Introduction

This is not the story of how my mother, my sister, and I escaped that catastrophe, of how the starliner Pegasus II tried to escape the disaster into FTL only to be destroyed by debris, of our flight to and rendezvous at the lifeboats, of the 24-person lifeboat jettisoning with just the three of us aboard. There are at least a dozen such accounts from the 87 survivors from the Peg, and most, to be honest, are more compelling. This is not the story of the first tumultuous hours after the...

4 years ago
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Lifes Strange Turns Part 2

Introduction: Youll want to read Part 1 first! Lifes Strange Turns, Part 2 The phone rang, waking both Karen and myself with a start. Wed slept for only about 15 minutes. Well, it would have been bad to sleep longer, but it would have been almost tragic if the phone had rung while we were writhing around having such marvelous sex. Especially if shed had my cock in her mouth I thought! To give Karen some phone privacy and to take care of some personal hygiene issues, I ran into the shower and...

1 year ago
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Confessions of a Sex Crazy Cross Dresser Part 2

Chapter 3: New York with Linda I didn’t really get a lot of time to think about what I had just done with Carlos. I fell asleep shortly after he left due to all the drinks I put away during the night. I actually fell asleep on my couch, still full dressed except for my jacket and shoes. When I woke up, I had a headache and was starving, I never even had a piece of the pizza Carlos brought. It was 2:00 in the morning and I was scared to look in the mirror. I took a shower to clean off the make...

4 years ago
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Boy Made Cross Dresser

Hi, I am a male of 32 years, but I like to cross dress. I used to work as a techie in a company in Bangalore but my love for a cross dress made me leave it. My parents broke relation with me when they caught me with my bf in college days and from then I am living alone. They don’t know even that I am alive or dead. This is my story of why I left my job. I used to work in this it company in Bangalore and my team leader was an arrogant person. I never used to get along with him. I liked to cross...

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