First Time As A Cd (real Story) free porn video

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this is a true story of the moment i first crossdressed to the moment i first had sex with another man dressed as a woman.

i was 18 the first time i dressed up, had been watching sissy porn for a while and fantasised about dressing as a girl and inviting a man over to fuck me. i went on amazon and ebay and looked at clothes, makeup, wig and heels. i would often do this, try to put together an outfit that looked sexy, slutty and most importantly feminine. i had just started the second year of uni and was living on my own, i had just received a lot of money for my birthday and decided that was time to give in to my fantasy and buy myself a nice bra and panties. i choose black ones, when they arrived i couldnt wait to tried them on, couldnt wait to find out how they felt. Amazing thats how, i went back online and bought more thing over the next few weeks.

i went a bit over the top and in a month i had apart from the bra and panties, a red bodycon dress that went half way down my thigh black heels, a blonde platinum wig, a makeup kit (with which i practised with as often as i could and got quite good with), some cheap jewellery and even got one of those breastplates (G-cup but i am quite tall so its not stupid big but still quite big). i was totally addicted to dressing up, everyday i would get home, dress up and masturbate.

one day masturbating stopped being enough and i started going on apps like grindr checking if anyone was around, and within 5 min of adding my photos and completing my profile i started getting messages. one of them was from a guy on his late 40s, quite tall bit of a gut and exactly my type. we messaged each other for a couple of days and agreed to meet at mine that night.

as soon as i got home i started getting ready, shaved myself entirely, got my breastplate and makeup on, panties, bra, dress and heels, the whole thing, even put on a sample from a perfume i had laying around. up to this point the only thing i had tried to put up my ass had been a small carrot so i was praying that he wasnt too big.

the doorbell rings, i get up and open the door and there he is, i let him in and he sits on the couch and i next to him. he starts telling me how good i look while touching my boobs and at this point my heart is racing. i explain to him that this was my first time ever doing anything like this, he tells me to calm down and starts kissing me. the kissing evolved into me lying on the couch with my legs over my head, dress pulled up and panties to the side while he rimmed me. I was in heaven, after a few minutes he stops and stands up, unzipping his trousers and pulling it out, rock hard, at least 7 or 8 inches, thick and veiny, i start to get nervous but dont let him notice it. i get to work and start sucking it, my first time sucking a cock and it was amazing, everything i ever imagined and more, i tried to deep throat it but i could barely make it half way.

a couple of minutes go by and his cock is covered in lipstick, i ask him to sit on the couch and get on top of him, cowgirl style and slowly try to get his cock in me. it hurt a lot so i put on some more lube on his cock and on my ass and give it another go, this time the tip goes in. i slowly work my way down, and manage to get it all in me. this is when he starts thrusting, slowly the pain starts to transform into pleasure and im bouncing up and down on him. we switch position, this time im on my 4s and he is thrusting away. i start to leak, the feeling is amazing and when i finish cumming i can feel my ass getting wetter and hear him moan, he had just creampied me.

i clean his cock up and he leaves, leaving me with the taste of his cum on my mouth and dripping from my ass.

i met him several times after this, if you wanna now the rest of the story let me know!

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10.08.2021
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Montreal 2

The following day being a Sunday, and as I had no plans for the day I kind of took stock of my situation. I had to admit to myself again that I not only liked the slutty life, but actually preferred it to the vanilla lifestyle. My ex husband had introduced me to it over the years, and we kind of lived a double life. Sex with him had been good, we did it in every imaginable way an in a multitude of situations. I'd often taken it up my ass to please him; he was often full of surprises that helped...

Montreal

The It was in the late nineties, 1998 to be exact and I was living in a small apartment in downtown Montreal. I'd been divorced now for over three years after 25 years of marriage. Thankfully my kids had been out of the nest and living on their own at the time of my divorce. Some think I was lucky as after my husband had taken off with a much, much younger woman, as I was left with everything. So after my divorce which was not contested, I was left with our house, the furnishings and our car. I...

Cinderella The Real Story

This is the second in my series of TG fairy tales in verse. The first, also available on FM, is: SLEEPING BEAUTY: The Real Story * CINDERELLA: The Real Story by BobH (c) 2007 He came to our town, a Prince from afar, Seeking a bride, her station no bar. Charming by name, he's giving a ball, He's invited our nobles, the townsfolk and all. My step-sisters have gone there, but sadly not me, Their hopes are quite high, though they're very ugly. Being a boy,...

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