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.