Ashley at Night Pt. 01

**Part 1 of a 4-part series surrounding Ashley's metamorphosis into the perfect sissy.

All characters engaged in sexual activity are at least 18 years of age.

This is a work of fiction. Names, characters, places, and incidents either are the product of the author's imagination or are used fictitiously, and any resemblance to actual persons is entirely coincidental.**

I'm Ashley. Well... that's not entirely true. By night I'm Ashley, but by day, my driver's license says Andrew.

In the day time Andrew works in a library. But enough about him - he's not me - not yet, anyway. In the day time, Andrew was the definition of normal - so normal, it was boring. Me, on the other hand... But I'm getting ahead of myself.

My story starts one year ago, when Andrew was in college. 18 years old, lonely, strung out from classes he could barely keep up with, he; like many before him, found decompression in porn. It started innocently enough. He was really into tits. He started by just googling that: 'tits', and then looking at the image results. Looking back, it was naive, but then again, Andrew had never looked at porn before. He had never touched himself before. He had never been with a girl before. but that would soon change.

Two, maybe three weeks in, and Andrew's porn searching skills had levelled up considerably. He lived with two roommates, and so kept confined to his room when his masturbation urge kicked in. It wasn't weird - his roommates did the same thing. What 18-year old didn't jack off in their room constantly? Only... they probably weren't watching the same thing Andrew was.

You see there's a subsection of the internet, in the far recesses of porn sites that catered to what Andrew apparently desired most. When he dimmed the lights and put in his headphones, he would grip his little cock hard and pump it vigorously to shemale porn. Or 'Tranny' porn, or 'Trans', or 'Femboy' or... 'Sissy'. That word stayed with him.

Sissies weren't always like other shemales: they didn't tend to have real tits (though, some did). And unlike most the shemale and tranny videos he found, where the tranny would fuck a girl or a guy with their great big cock, a sissy represented the submissive side of the trans spectrum.

He didn't know if it was the baby blue and the hot pink that got him excited. Or their need to be the nastiest, horniest bitches around. Or maybe it was how some of them wore cute pink plastic chastity cages - locking up their cocks to forever forget they were men.

Gooning was a phrase he would learn much later, but oh he became a gooner alright! It wasn't even a month in before he started experimenting. And it was around that time that I come into the story.

Andrew was a pretty boy. Thin, hairless... with his small prick, girls thought he was still developing, but no - he was just born that way. Where Andrew failed as a boy, I thrived as a girl. A sexy trim figure, easy to hide what was my cock... I quickly began accumulating an array of sexy panties and lingerie that Andrew fetched for me in the day. It didn't take long until he braved into more adventurous stores, and that's where the real fun began.

Valentines day. That was the day I think I became me. Andrew had come home with a large brown paper bag filled to the brim with objects of a perverse nature. His favourite: the cage. He couldn't wait to try it on. It was pink plastic, like the ones he'd seen in his porn videos. Me, however... oh, it was the big fucking animal dildo that he'd buried to the bottom of the bag.

In the shop, he had blushed so much buying it, but as I held all 10 inches of it in my hands, I had no such embarrassment - I knew I must have it.

Flash forward to a month later - I was completely alive. The clothes, the toys... it all got a bit pricey, and I thought what better way to pay for them, than by starting my very own onlyfans page.

I did... ok. Truth be told, it's a limited market. But it did pay for Andrew's hobby, and my new nighttime lifestyle. Three times a week I went on cam, one night I would focus on my own pleasure, and the other three nights I would be out on the town. Initially it started as just going clubbing. The confidence I had leaving Andrew's room each night... On the third time, one of his roommates caught me, but with how I looked, he didn't even see the resemblance.

Let me explain: After hundreds of makeup tutorials, and a bank account dedicated to looking the part, I looked about as much like a boy, as Aphrodite, herself. I had a theme, of course - each night it changed. I liked the little prissy pink sissy the best, but a sexy black dress, or smoking hot red also did the trick. At least a few times I dared leave the apartment in nothing but a latex minidress (far too small to cover my shame).

After the first few weeks, I got a little bored of clubs. It was exciting at first, mind. My first kiss was with a boy in the bathroom, his little hands feeling up my ass and squeezing my fake tits beneath the padded bra. My next four experiences were all similar - I wasn't as loose at the start. On the fifth boy, however, oh he tasted so good. He told me to get to my knees in that filthy club bathroom - not asked, like the others: no, he told me. I did what he said like a good girl, and like a not-so-good-girl, I showed him everything I had learned from deepthroating my dildos at home and made him cum all over my pretty face, spurt into my open mouth and dribble it down onto my dress.

When he was done, he told me to get up. I did so, heart pounding. He inspected my cum-covered face and smiled, telling me to go back out to the dancefloor. Never before had I experienced such power in a man... I did what he said, and minutes later I ran into what would soon become my best friend.

Lucy - wearing a sleek red dress, with a plunging neckline almost inviting me to nestle between them. She took one look at me, the lights dancing off my glistening face and pulled me close. The cum from my dress smeared onto her skin, and she kissed my cheek, squelching her face against mine.

By the end of the night we were in the girls bathroom playing with toys from her purse. The cubicle next to us sounded like they were doing a similar thing. Lucy didn't mind that I had a cock - in fact, she found it sexy that I locked it up. She offered to peg me like the dirty bitch I was - an offer I would take her up on many many times.

But the nights were short - only so much time, and as much as I like dancing, I liked being a slut so much more. That's when I slid into Grindr.

It wasn't my first time a dating app was on my phone. Andrew had tried Tinder for a while, but never so much as a kiss from a girl. A few weeks in and I'd already stuffed toys into a welcoming snatch - being a girl was so much easier.

Grindr culture, wasn't like Tinder, though. Tinder was all about dating. Grindr... Hooking up was always implied.

My first 'date' was with a guy called Terry. 5'11'', muscular, 8'' cock... or at least that's what his profile said. He had complimented me on my pink thong panties in my profile picture. He asked to see the front, so I sent him a pic.

A cage!! He became very excited. I suppose if that didn't label me as a bottom...

That night we met in the park. We didn't make it much farther. He was so authoritative. I was on my knees in seconds. I was bent over in a bush minutes after. Thank god I had practiced... he may not be the full 8'' he had promised me, but he was relentless. When I got home, I stripped and headed into the shower. The cum dribbled out and down the drain.

During the next few months, I met with dozens of men. Some more charming than others, but all motivated in their rearrangement of my insides. That latex outfit I mentioned? - that one was for a particularly kinky gentlemen: Gareth. He got off on having me exposed, my caged cock just visible as we walked through the club. He's how I got into calling each of my partners 'daddy'. He said he liked it, and honestly... so did I.

Eventually, Andrew's flatmate asked him about me. Andrew (as to be expected) panicked. He explained that I was his girlfriend, but that we weren't public about it. What a little cutie...

I suppose the story was harder to explain when a few weeks later I brought someone home. Mr Panther. He was our professor, and married. Finding him on Grindr was completely by accident. I didn't think he knew I was a student until I brought him back to my apartment.

Having snuck him in my room, I told him we should be quiet. He looked at me pondering to himself. I think he was trying to decide whether or not to leave. Whilst he was deliberating, however, I bent over deep, reaching to the back of my bottom drawer. From behind my pink thong, I knew he could see the thick black butt plug stretching me out. I turned back around, the big fuck-off horse dildo in my hands. I had mastered it by then and I wanted him to know how slutty I was willing to be for him... as if my pink petticoat and painted face didn't already tell him so.

I told him to be quiet, but it was me who screamed like a little whore. He teased me, pleased me, stimulated me and stretched me until I was begging him to let me cum - something that if he hadn't told me not to, I would have done an hour before through my cage. He held my chin in his hand and instructed me to cum only when I made him cum.

I rode him like the playboy bunny I embodied to me. I spoke filth to him that would have had Andrew's parents disown him. And when he finally erupted deep inside me, I too spurted out of my teeny tiny cage.

I lay with him for a solid 30 mins, covered in both our cum. He then stood up. I begged him not to leave me. I had never been with a man like him, and I would be damned if I let him leave to go back to his ungrateful wife.

He gave me a promise, on a condition. He promised me that he would give me everything that I wanted - everything that I needed to be who I was meant to be. I was elated at his words. And then he told me the condition: I would be his - just his. I was to stop meeting men without him.

Without hesitation I agreed, lunging forward to grasp at his leg, reaching up to tongue his sweaty balls and lick up his long shaft. He smirked and stroked my hair as I tasted the tang of my own asshole on his cock.

That was only the start... that was about four months ago. And so much can happen in four months...