A Sissy Slut's Diary Ch. 03

I was awoken by the musical beeping of my phone's alarm at 7am, and was met with a flood of memories of the night before, of taking a stranger's cock and loving it. I couldn't help but break into a grin as I lay there filled with a warm mixture of satisfaction and pride and arousal, and also nervous anticipation. I had made plans for today, I knew, so I had sixty minutes until I would get to experience it all over again.

Pulling off the socks I'd slept in, I clambered into the bathtub and ran the shower. I had brought a razor with me and quickly shaved my body again, not so much out of necessity as out of a continuing desire to be as perfect as possible. I hadn't eaten since the morning before, unless you counted swallowing a load of cum, but still took the effort to clean out my ass before jumping out of the shower and towelling off.

Naked, I stood before the mirror in the room admiring myself. A little taller than the average girl admittedly, but I couldn't deny that even without lingerie on, standing there nude and smooth I looked damn feminine. Slim, long legs, a tight little waist, a smooth round ass - I really was born for this.

Having dried off I finished getting ready, teeth brushed and a spray of a women's perfume of a brand I never heard of that I'd picked up from a store a few weeks ago. The cashier has asked if it was a gift for someone special, and I had just nodded. I supposed it was though - it took a special girl to get this kind of action after all, two guys in the space of 12 hours. I had 35 minutes until David would be here.

From the wardrobe I selected my outfit for the morning: a black lace teddy, under which I wore a pair of equally lacy black panties to tuck my dick into to keep it from flapping out the side. I was decked out in black lace, with my usual mask on, and a pair of hold-up stockings with lace tops. I slid my feet into my heels and snapped a couple of photos in the mirror - one bending over slightly to show off my ass, another showcasing my legs as I adjusted my stockings. I sent both to David, who quickly replied. "Fuck you're such a slut." I blushed.

I sent the same pictures to William who I had met the night before, teasingly asking if he was jealous he wouldn't get a chance to play with me again today. After last night I was brimming with confidence it seemed, and he quickly replied also. I almost thought to invite him around this evening, but he quickly mentioned he was busy - he was going on a date, he said, but he knew he'd be thinking of me while he fucked her. All I could do was smile.

A knock at the door, as always, made me jump. I quickly glanced at my phone - 7:42am. He was early. I hadn't even had time to warm up my ass with my toys, although I supposed I might not need it after the workout it had last night. It ached a little, I realised, but was impressively not that sore. I jumped up to check through the peep-hole that it was indeed David, and opened the door.

He definitely wasn't as handsome as William, probably in his late thirties, thinning on top, and carrying a little extra weight. But I knew it didn't matter - it was his cock I was most interested in. I closed the door behind him as he entered, and he wasted no time. The door was barely shut before he was unbuckling his belt, and sliding his jeans to the floor. Through his boxers he ran a hand along the outline of a huge cock, and I dropped to my knees, neither of us having spoken a word. He sat himself on the edge of the bed, trousers at his ankles, and I shuffled towards him, my eyes fixated on his bulge. He let go of it himself, and my own hand reached forward, feeling it through the fabric of his underwear. It wasn't even fully hard, and it was already big. I pulled the waistband of his boxers down, and enjoyed the incredible sight of it bursting out of them and waving slightly in the air, semi-erect before me. One hand went to the base, and another to the shaft, and my lips moved straight to its head.

I ran my tongue along his head, running across it in circles as my right hand slowly stroked it up and down. I could feel it still hardening in my hand, growing even more and quickly realised just how huge it was. I had definitely never taken anything so long, or so thick. Even his head was huge, mushrooming out so big I struggled to take it in my mouth, fearing my jaw wouldn't open wide enough. He had no such reservations, grabbing the back of my head to push me down onto it. This wasn't the first time someone had done this to me, but it was the first time I'd choked on a cock so big - my gag reflex kicked in immediately, and with my eyes watering I pulled my head back, choking and spluttering trying not to heave, which I figured wouldn't be an attractive sight.

David figured no such thing - he quickly grabbed my head and pushed me down onto his cock again, forcing my jaw to stretch so far it hurt trying to accommodate his massive member. I felt a tear drip down my face as I tried without success to fight the impulse to gag as his cock slid across my tongue and forced its way to the back of my throat, and he pulled out again leaving me to heave and choke. With a shock I felt his palm slap my cheek, leaving a stinging feeling and startling me out of my gagging. A strong hand gripped my throat, and lifted my head up to look him in the eyes.

"Suck that fucking cock bitch." Eyes wide, I nodded. His hand released my neck and I quickly went to work on his cock. I had covered it in spit from choking on it, and used my right hand to stroke it as I sucked on the head, picking up the pace as I sensed he liked it hard and fast, not shying away from being aggressive. A few times I tried to push it further down my throat and each time came up spluttering, each time met with an appreciative moan that kept me pushing through the discomfort. There was definitely not much physical pleasure in getting my throat fucked, but there was a feeling of pleasure from pleasing someone in spite of my own pain or hurt, an amazingly slutty feeling to knowing what I want didn't matter, all that mattered was that he used me and enjoyed it. The limits of that feeling were soon to be tested, but I didn't know it and focused on how amazing it was to be sucking on something so huge - I couldn't even wrap my hand all the way round.

Abruptly, a hand came and once again slapped me across the face, causing me to drop his cock from my hand. David reached beside the bed where I had left some stuff at the ready, and grabbed a condom and tossed it to me. I unwrapped it, pinched the top, and with nervous hands slid it down his cock - the first time I had ever put a condom on anyone's dick. I hadn't even worn one myself, and here I was preparing a cock as thick as my wrist to fuck my tight asshole. My stomach was churning, but I knew there was no backing out now - not just because I didn't think he'd take no for an answer now, but because I knew I didn't want to say it.

David grabbed my waist, and tossed me from where I sat onto the bed beside where he had laid, so my head landed on the pillow. Lying on my front gave him a perfect view of my ass and his fingers went straight to the fabric of the teddy, sliding it to one side along with my panties to give him a view of my hole. I hadn't considered how awkward it might be to wear these two layers, and he quickly let go of the fabric and grabbed my shoulder with one hand, pulling me up onto my knees.

"Take this shit off," he told me, pulling at the back of my lingerie. I obliged, untying the fastenings at the back of the teddy and letting it drop down, shimmying it and my panties down my leg, leaving me suddenly worried I didn't look girly enough any more, nude but for a wig and stockings. David yanked the lingerie down my legs though and tossed it aside, obviously not off-put, and shoved me back down onto my front. I felt the bed shift as he reached over for the lube I'd left on the side table, and heard the sound of him squeezing the bottle and getting his cock slick and ready to fuck me. A few cold drips dropped onto my ass and made me shiver, and I expected him to push a finger inside of me, to get me ready to take his big cock. It didn't seem he was interested in wasting time with that though, as he placed a hand in the small of my back and pinned me down, his other hand sliding my ass cheeks apart as I felt the cold lubricated cock slide up against my hole. Slowly he pressed in and I buried my face in the duvet as I cried out, trying to stifle my own shouts of discomfort as he forced his huge head into me.

It was here I was grateful for the night before, because I had no doubt that if my ass hadn't been stretched out and fucked so recently I never would have been able to take him inside of me. As it was he was really stretching me out, sliding into me regardless and I cried out again as he pushed deeper than I'd ever taken a cock or toy before, feeling him press against my insides in a way I wasn't sure I liked. Still, I wasn't going to tell him to stop, I wanted him to give me every inch - both because I knew that's what he wanted, and because I needed to feel what a truly huge cock felt like inside of me, to feel like a proper pornstar slut. There are some moments that truly rid me of any doubt I might have about whether being a sissy is what I truly want, and this was one such moment as I realised how thrilling it was ton have him push his full length into me as much as it hurt.

With his hand still firmly pressing me to the bed all I could do was lie there and appreciate the helpless feeling of having his weight bearing down on me, his thrusts gradually beginning to pick up speed and truly fucking me. I had just begun to relax into the feeling when I felt the palm of his hand come down hard on my ass, making me tense up and cry out as he left my ass cheek stinging, and I didn't have a second to lose that tense feeling before he struck me again, spanking my ass hard enough I could hear the slap of skin echo out, not for a moment easing up his pounding as he continued to slap me, making my eyes water. I could hear him laughing, telling me I was a filthy little faggot, and I felt myself blush red in a way different than I had before when a man had called me names. I'd always felt flattered and proud to be called their good girl, proud and dirty to be told I was a good slut, but to be called a faggot made me flush with shame and embarrassment. I supposed that's what I was, after all, it drew me out of my fantasy of being a girl lying here taking this cock and reminded me I was a boy after all, a boy dressed up in a wig and stockings letting a man fuck his asshole.

At first the feeling was one of being small, pathetic, ashamed, but it wasn't all bad. After all, he wasn't stopping fucking me - I might be a little cocksucking fag, as he told me, but he still wanted me, was still enjoying fucking my ass, and that's what mattered to me. Something about breaking my perfect feminine fantasy was actually exciting in a way, reminding me that other guys I knew were out fucking their girlfriends, while I lay here letting a stranger use my ass and mouth. My tender ass still stinging even as he grabbed my waist in both hands reminded me just how little it mattered to him if I enjoyed this, and that only made me love it even more in spite of the pain of him stretching me out as he fucked even harder.

I moaned and whimpered into the bedsheets as his pounding became more furious, more intense, making me truly ache and hurt as all I could do was shut my eyes tight and listen to the sounds of his heavy ragged breathing and his skin slapping against mine. It was sudden when he pulled out, jumping off of me and flipping me onto my back. I looked up at him startled, and watched as he tossed the condom aside and grabbed my jaw in one hand, sliding two fingers between my lips to pull my mouth open wide as he knelt beside my wide-eyed face, stroking his cock for only a few seconds before I felt cum spray across my face, some landing in my open mouth and more covering my nose and cheeks. His fingers pulled out and he pushed my jaw shut, and instinctively I swallowed the cum in my mouth and smiled at the taste, salty and slightly unpleasant but still wanting to be the good sissy who swallowed every drop she was given.

David squeezed my cheeks together. "You like that you fucking slut?" I couldn't open my mouth so just nodded, and he shoved my face aside and hopped off the bed. "Clean yourself up, I'll be back this evening."

I propped myself up against the pillows, still feeling the hot sensation of his cum on my face as I watched him dress himself, my ass aching so much I felt sure I'd look down and see blood on the bed, but thankfully being mistaken. He headed straight out the door without so much as a goodbye, and I was left there, lost for words and still tasting him in my mouth.

--

I sat on the floor of the bathtub as the shower ran over me, washing clean my face as I pulled my knees to my chest and thought about what had just happened. It had been exactly what I had expected right until it hadn't, and really it was only those few words that had me reeling. As I remembered the feeling of him inside me I felt myself getting hard, but I knew if I came then I would lost all desire to meet him again tonight, would fall into the pit of shame I was currently teetering on the edge of. Instead I simply sat there for a while, before eventually towelling off and staring at myself in the mirror. I hadn't really let my sexuality enter into this, I realised, always somehow separating my usual self from how I was when I dressed up. I was attracted to girls though, I knew, I would see girls on my course I wanted to sleep with, to fuck. But that part of me that wondered what it would be like to be in their place had gradually come more and more to the forefront. When was the last time I even watched porn and imagined myself as the guy? I couldn't recall.

Looking at myself stood there naked I knew every guy that fucked me knew that no matter how feminine my frame, how smooth my legs, how girly I dressed or how good I sucked cock, I wasn't actually a girl. But still, as I slid a pair of stockings up and stroked my nylon-covered legs I knew I didn't care. Male, female, it didn't matter, all that mattered was how good it felt to dress like this, to submit myself to a dominant man, to be fucked. I sat in front of the mirror feeling my little cock now rock hard as I pulled on a pair of cotton panties and a little black bralette, and stroking myself for only a brief moment before pulling on my regular clothes over everything, and heading out to get lunch, and also the wine I knew I would need if David was truly coming back this evening.

There was always a special thrill to knowing I was wearing panties or stockings underneath my clothes, and as I walked down the street all I could do was notice how many gorgeous girls walked around dressed in outfits I could only dream of heading outside in. They had it so lucky, I thought, to be able to just slip on a tight dress and a pair of heels, to have every guy's eyes on them. Looking at the men all around me I could only imagine what they would think if they saw me back in my hotel room with a wig on dressed like a schoolgirl or in a lacy babydoll with matching stockings, By the time I was paying in a store I don't think I noticed a single girl around me, all I could think was how big the guy at the checkout's cock might be, what it would feel like for the man queuing in front of me to bend me over the edge of the bed. I headed back to the hotel with my heart pounding, knowing the evening couldn't come soon enough.

--

He'd be here at 7, he messaged me, and at six I'd sat all dolled up with a mug of white wine in my hand. As 7 came around I dropped him a message but got no reply, pouring myself another drink from a half empty bottle and fearing that this was yet another no-show, another time I was sitting ready to be fucked only to end up disappointed. By the time it was 8 I had finished the bottle and laid in bed, scrolling through Grindr with one hand while holding a second bottle of wine in the other, sipping straight from the bottle. A couple of guys messaged me asking to meet tonight, but neither was remotely what I was looking for. After this morning I had prepared myself to be degraded, to be fucked hard by a huge cock again, not to meet a man four times my age who called me princess and sent my grainy photos of a cock as small as mine.

When the knock came I practically jumped out of the bed, rolling the wine bottle under the desk and tossing my phone onto a pile of folded clothes in the wardrobe, quickly eyeing myself in the mirror as I straightened my stockings, neatened my wig and took a deep breath before opening the door. David walked straight in without saying a word, shoving me backwards onto the bed. It was exactly what I'd been waiting for, and I lay there watching as he pulled his shirt off and dropped his pants, grabbing my head and pulling me down to suck him. Some part of me was still pissed off he hadn't messaged me to say he'd be late, but I tried to push that aside as I reached out a drunkenly shaking hand and grabbed his cock, stroking it and smiling up at him before taking it between my red painted lips. His hands grabbed either side of my head and held me there with my back against the side of the mattress, letting him thrust towards me and fuck my mouth, robbing me of all control of the situation, forcing himself deep into my throat. I tried to push him back but his grip was solid, forcing himself deep enough into my throat that when he pulled back he left my gagging and fighting the urge to throw up, drunk enough that it was a real struggle. I was about to ask him to go gentler when he grabbed me again, pushing me back and once again sliding into my mouth, making me heave and tears stream down my face as he fucked my throat.

As he pulled back this time I had to lunge to one side out of his grip, feeling certain I'd be sick but knowing I couldn't be, that I had to fight my gag reflex for him, telling myself to relax and try harder to be the kind of girl I dreamed of being. He didn't grab my head again, but stood before me and let me crawl back over to him, let me grab his cock with one hand and push myself down onto it, feeling it slide across my tongue and down my throat, making a conscious effort to relax myself and fight any instinct to choke, wanting to take him as deep as I could. There was no chance I was taking every inch in my mouth but I did my best, hearing him moan appreciatively and feeling flushed with satisfaction.

By the time he was clearly ready to fuck me I didn't wait to be thrown around, I just spun around to bend myself over the edge of the bed, arching my back to wiggle my ass at him, no doubt showing well beneath the short skirt I had wore without anything underneath it. David's hands stroked my cheeks, and then I saw as he darted over to grab the lube, squeezing it out straight onto my hole. I moaned from the touch of it, and heard him laugh.

"You're such a fucking slut," he said, and I just smiled and rested my face on the duvet.

His cock pushed into me, easier than it had done this morning but still with enough strain that I bit down on the bedsheets, bracing myself and powering through those first painful minutes as I felt sure he was going to tear something inside of me. His hands were on my hips as he thrusted into me, each time slamming me into the bed-frame and making it shake, and soon I began to moan as he did so, first from discomfort and then, as I knew from before I would, pleasure too. I wished I had angled myself by the mirror, knowing how incredible it would have been to see myself here bent over like this, with a man's hands holding me tight as he pounded away at me.