Sissy fantasy to reality

Like the majority of my stories, this one begins with alcohol and a hotel room. But really it begins several months before that. Ever since I was 18 I had been dressing up in some way, starting off with just wearing panties from time to time. Soon I ordered a butt plug and some lube online, and would watch porn imagining I was the one taking those big cocks. It was only when I turned 19 though that I really got serious about it - having just started university, I was one of the only guys on a course full of girls, and spent my time in lectures alternating between fantasising about sleeping with the girls around me, and fantasising about being them.

One girl in particular really caught my eye: Isabella. She was definitely gorgeous, but what I noticed most was the way she was dressed - she clearly dressed herself every day with the express goal of being as sexy as possible. Skirts always short enough to flash her ass, her legs always looking incredible in knee socks and stockings, showing off her figure in crop tops and skinny jeans. I mean this girl wore high heels to early morning lectures, she went all out. She was teaching a master class in feminine perfection, and you better believe I was taking notes.

Within a few months of being at university, I began starting my own girly wardrobe, inspired by Isabella. First: stockings, garter belt, matching lacy panties. A black set, then a white. Next came a wig - wavy brunette hair, just like she had. Next up a short little skirt, a tight button up shirt. Calvin Klein bra and panties. Knee socks, sheer tights, patterned tights. A lacy teddy, a camisole, babydoll, a pair of heels. I remember sitting at home, legs shaved smooth for the first time, stumbling in heels I'd never worn before, and seeing myself in the mirror - I already had a slim frame, but the heels made my legs look even longer and more feminine, and with the way the lacy teddy hugged my ass and the wig fell down my back.. well, I looked like one hot girl.

For months that's all I'd do - dress up girly when no one was around, maybe snap some photos, and eventually graduate from a butt plug to a dildo and watch porn while struggling to take 6 inches in my very tight ass. Pretty soon I was posting pictures of myself online, face cropped out, showing off my round ass, and loving the attention from guys who didn't hesitate to tell me what they'd do to me if I gave them the chance. For years I'd thought about meeting someone, joined hookup sites and dating apps, but never felt comfortable meeting someone - I was worried I wouldn't be girly enough for them, or that I wouldn't enjoy it, or that I wouldn't be safe. But mostly I didn't have the opportunity. That's where the hotel room came in.

The first time I booked a hotel room was a big disappointment. I had found somewhere in a city near me, very cheap for the night, and taken a bag of girly clothes with the excuse to my family that I was staying with a friend. I checked in and within minutes I was fully dressed, admiring myself in the mirror, heart racing with the thought that soon someone could be in this room wanting his cock inside of me. I remember lying on the bed, scrolling through Grindr messages that were 95% gross guys, and filtering through to find the few truly hot ones whose dick pics had my mouth watering. I had checked in pretty late, and soon began chatting to one guy in particular - he was gorgeous, with an incredible gym-fit body and a cock made for porn. Despite my early evening check in he wasn't free for a few hours, but he wanted to come to my room later that night and find me waiting on my knees for him. I'd never been so turned on, or so nervous.

After a few hours of anxious anticipation, he texted that he was on his way and in twenty minutes he'd be outside my door. It didn't really occur to me at the time that a) I'd picked a hotel where you needed a key-card to get from the elevator to the rooms, and b) I'd have to let him in so he couldn't find me on my knees waiting for him. All I could think about was how excited and terrified I was. What if he saw me and laughed? I'd never let anyone see me dressed up before, except in photos. Maybe he'd think I wasn't girly enough, maybe he'd just not find me attractive. Maybe I wouldn't find him attractive. What would I do, ask him to leave? Soon I'd been waiting thirty minutes, and I texted him to see if he was nearly here. Forty minutes passed, then fifty. I checked back on Grindr, and his profile was gone - he'd blocked me I supposed.

There was admittedly a part of me that felt relief, but more than anything I was disappointed. This was the first time I'd actually come all this way, got dressed up, even douched my ass multiple times just in case, and arranged to meet someone, and without any excuse he just didn't show. I checked back on Grindr, debating whether to invite someone else. It was pretty late now though, and the first guy I found who seemed exactly my type told me he'd love to come round, but it would have to be tomorrow night. Another guy sent me a video of him stroking his cock, which had to be 9 inches long and had my absolute attention - but told me his wife was sleeping next to him, so we'd have to make plans another time. I had more messages but didn't bother reading them - my urge to meet someone had faded, I felt more sick than excited, and so I ended up deleting the app, taking off my girly clothes, and just going to sleep.

If that sounds like an anticlimactic end to the night, it definitely was. But it taught me a couple of things - first, that making plans ahead of time is always better than hoping to arrange a hookup within a few hours. Second, that my nerves get the best of me if I wait too long. Lastly, that I wasn't confident enough in myself yet to truly get excited without worrying too much about it. The first problem could be solved with some simple preparation ahead of time. The latter two could be solved with a little liquid courage, and I would learn, the right guy.

*****

It took several weeks before I ended up dressing again. This was just before Craigslist scrapped its Personals section; I remember that because I had temporarily eschewed Grindr for anonymous posts on there, deciding that emailing someone led to a better chance of feeling comfortable with them than the rapid fire message to hookup speed preferred on the app. I had been emailing a few guys, some whose ads I responded to, some who responded to ads I posted. All pretty straightforward posts - a couple of pictures of myself, showcasing my bubble butt and hiding my face, and explaining I was a wannabe sissy slut looking for someone experienced for my first time.

To save retelling another story without action in full, I ended up with another disappointment. My family were away for a week, and one evening I decided to invite a guy round that I'd been talking to - he seemed amazing, with a gorgeous cock, and an amazing body, although I hadn't seen his face. More importantly though, he was able to both turn me on and put me at ease - he was dominant, which I loved, but not aggressive or rude, and made it very clear that things would go at whatever pace I was comfortable at since it was my first time taking a real cock. Or rather, would have been had he shown up, which he didn't.

This time though, I'd been drinking some wine while emailing him, and realised the nerves has been dampened and given way to sheer excitement. It was certainly the key to meeting someone. I ended up keeping in contact with someone else from Craigslist who I did end up having a very hot meet with, a story I'll post another time, because before then I was back on Grindr. It was a week after my parents returned, so I was back in a hotel room. This time, I'd talked to the guy for a few days beforehand - he was very hot, and very into me. He told me what hotel to book that didn't require key cards to get to the room doors, and more importantly told me what to wear. I bought a schoolgirl outfit especially for him - he wanted me in white stockings, white heels, a red schoolgirl skirt, and a crop top. I couldn't help but think of Isabella when I saw myself in the mirror, shirt too short to cover my whole ass, a black thong just visible between my cheeks, and legs clad in lace top hold ups. I'd tied my wig into pigtails to complete the look, and wore red lipstick and a lacy black mask - I'd gotten it for free with a teddy and sent some pictures wearing it, and he loved the look of it. It also helped hide the fact that, lipstick I stole from a friend aside, I knew nothing about makeup.

He told me he'd be outside my door at 8, and I had three glasses of wine before then - it settled my nerves, and had me aching to feel his cock inside of me. Unfortunately just before 8 he told me he'd be late, and I suspected he wasn't coming. I had drank the other half of the bottle by 8:45, when there was finally a knock at my door and my heart almost jumped out of my chest. I remember my head swimming a little as I stood up, and would later think it a mistake to drink so much, but in the time it definitely felt like it helped. I opened the door to find him standing there - he was the same height as me, which I probably would have found disappointing if I'd been able to think straight at the time. I let him in, and the door shut behind him, and I could feel my little cock straining against the panties. I forgot to even worry about what I was wearing - the though of how I might look disappeared three glasses of wine ago.

I remember standing there as he came in, took off his jacket, and revealed very muscular arms. He'd already said he wasn't looking for any kissing, which suited me well because I wasn't yet sure I wanted that - I knew I wanted to be fucked by a man and that was all so far. I jumped a little when he walked over and slid his hand under my skirt on my bare ass. He whispered in my ear that I looked like a perfect little slut, and I felt myself melt a little. He squeezed me ass and ran his other hand up my stomach, stroking my chest and my nipples, which made me shiver a little - I'd never had anyone touch my this way before, and the feeling of his hands, still cold from the outside, sent tingles across my body.

He leg go of my ass, and swiftly kicked off his boots. He seated himself on the bed and pulled his trousers and boxers down in one movement, and his cock bobbed there before me. He pulled himself to sit on the bed's very edge, and wordlessly I knelt before him. His cock definitely wasn't as big as he'd said - I only had my six inch dildo for reference, but it seemed the same size, if anything not as thick. Of course I'd realise this wasn't a bad thing - jumping onto an eight inch cock for my first time probably wouldn't have been too clever an idea - but it was still a little disappointing, although that quickly passed aside as I apprehensively reached out my fingers to touch it. I remember that it only took a few seconds before he told me to get my lips around it, and I obliged. It was surprising how different it was from sucking on a dildo - I'd taken a video once of my sucking a dildo to send to a guy, and had thought at the time that if sucking a real cock was like that it would be kind of unappealing. This though was totally different - feeling it, warm and throbbing, hearing him breathing heavily as I ran my tongue across its head and down the shaft, gently kissing the tip before taking it between my lips and taking it a few inches in my mouth. I knew I had too much of a gag reflex to try and deepthroat it, but he didn't seem to mind.

He laid back as I began to get into what I was doing. It's not like it tasted or felt amazing physically, but the psychological side of it was amazing. Looking up at him laying there, feeling him moan and respond as I took it deeper into my mouth, one hand stroking the base of the shaft as I sucked. Just as I was really feeling like I was getting into it, I felt his hand on my head pushing me back. I was a little startled, but he stood up and pulled his trousers off completely. I had been hoping he'd be more physical, pick me up and throw me onto the bed, but instead he just asked me to lay down, so I did so - first laying on my back, before realising he meant to lay on my front and flipping over. It was at this point I noticed my heels beside the bed, realising I had forgotten to put them on like he'd asked, and briefly felt embarrassed and apologised, but he told me it didn't matter. It might have felt reassuring, but mostly it made me realise how unprepared I was. I was lying there, unable to see his face, and feeling him moving around on the bed behind me. I had told him my biggest fantasy was to just be pinned down and fucked from behind, pounded into the bed, but it was quite a discomforting experience, laying there waiting until a hand on my ass once again made me jump.

I know we'd discussed using a condom, but I didn't have the nerve to turn around and ask if he was wearing one. I also didn't really care as I felt a hand pull my thong aside as a finger, thankfully slick with lube from the bottle I'd left beside the bed, pushed between my cheeks and touch the opening of my hole. I instinctively felt it clench shut and had to take a moment, breathing heavily with anxiety, to relax myself as he touched the opening with one hand and spread my cheeks with the other. I'd left a butt plug next to the lube and know he'd mentioned wanting to use toys on my ass, but that had clearly gone out the window as I felt first one finger slowly push inside of me, then another. Like sucking cock, it was a shockingly new experience - when playing with toys I'd loved the feeling, but it had been predictable - after all it was my own fingers entering me, or moving the toys, but here I had no idea what to expect, and each movement was a surprise.

After a minute, hands lifted my waits slightly and my thong was slid. I could feel his hands stroking down my stocking clad legs, and then back up before gripping my ass, more firmly this time. I pushed my face into the bed to stifle my ragged breathing as he stroked my cheeks, tapping them very lightly in what might have been meant to be a gentle spanking. It was quickly followed by the sound of more lube being squeezed from the bottle onto what I would quickly realise was his cock, as I felt it press against my hole. His legs straddled mine, and one hand spread my cheek to the side as he gradually pushed his head inside of me. It was a tight squeeze. I usually spent a while working myself up from fingers, to plug, to dildo, and even though I could take that it wasn't with ease. He was definitely not as thick as that, but the initial sensation was definitely an uncomfortable one as he slid a couple of inches inside of me. He pulled out, and thankfully squeezed out more lube, before again pressing inside - I still had no sense of whether he was wearing a condom as he slowly and steadily slid in deeper, until I tensed up from the discomfort, and he pulled back slightly, before building up a gentle rhythm in and out. His hand pressed into the small of my back, and he slid in again until I moaned from the feeling of him going deeper inside me. I could hear him, talking softly not in my ear but just out loud, grunting and saying how good I felt, and I immediately felt better about the whole thing, even more so when he picked his speed up a little and called me a "good girl", telling me to "take that fucking cock baby". If there's one thing that always gets me into someone it's them calling me a good girl, or a good slut - nothing like a little praise and humiliation coupled together.

I had really been hoping he would flip me over and fuck me missionary - I had seen his pictures and how amazingly fit he was, and wanted a chance to get my hands on his muscular body. But I was happy enough to have to settle for being fucked from behind more. He pulled out of me, and grabbed my waist to lift my up onto all fours. I did my best to arch my back, which I'd seen advised in so many sissy guides, and his hands gripped my waist as he pulled me back onto his cock. He was obviously getting more into it, thrusting faster, which had me biting my lip in discomfort - he wasn't going that hard or fast, but it was still way more than I was used to. If he'd been the full eight inches he'd said I think he'd have had me moaning in pain, but instead I was just somewhat uncomfortable. It was offset though by the feeling of being fucked like that: my body rocking back and forth as he thrust into me, my cock was now soft from the confusing sensations but it didn't mean I wasn't turned on. I felt the girliest I had this whole time - being gripped by a man who was pounding me from behind, occasionally repeating the same few praises - that I was a good girl, telling me to take it all, and saying how good it felt. I definitely flushed red at each compliment, my head spinning a little from the wine and the whole experience, as he pushed me back down flat onto the bed and his rhythm slowed. I didn't even realise he'd came until he pulled out - he had indeed been wearing a condom, which I saw him toss onto the floor, missing the bin underneath the desk beside the bed.

We hadn't talked about what I wanted - I made it clear I wanted to get him off and him alone, there had been no talk of me finishing, and I was glad for it. I felt myself getting hard again as I lay on the bed, watching him redress. I lay on my side as he pulled his jeans back on, and I could feel lube dripping from my ass, which was feeling increasingly sore, and held in the rather unattractive urge to push it out. Across the room, he sat himself on a chair rather than the bed and pulled on his boots, and I stood up, not really knowing what to do now. I've found it pretty rare that a meet ends without a moment of awkwardness from someone, but he seemed more sure of himself than I, and I headed over to get the door. For a final time, he made me jump a little as he squeezed my ass, and not knowing what to do or say I just thanked him, which was met with a laugh and a simple goodnight as he left.

I remember feeling kind of at a loss for what to do now - I just laid back in the bed, and gingerly touched my sore asshole, which I knew I wouldn't be able to play with for a few days at least. I ended up lying on the bed, touching myself to the memory of it and the feeling of his cock that still lingered inside me, before cumming over my skirt, taking off that, the wig, the mask, and shirt, and falling asleep wearing only a pair of stockings, smudged lipstick, and a smile on my face.

It had been several weeks since I'd taken my first dick, and I knew I wanted more. I had struggled to find time around university to arrange anything, but soon had a long weekend coming up and I knew I had to make the most of it.

I had the basic plan worked out - I'd tell my parents I was staying with a friend from uni for a night, then call them the next day to say I was going out again and staying a further night. I knew it would look suspiciously uncharacteristic of me to plan to stay two nights with someone, but a last minute decision to go out drinking again? That was very much me.

Of course the real plan was to get a hotel room. Two nights, so many possibilities. I had chosen the cheapest places available before, but went for somewhere a little pricier this time. The need for it to be somewhere that didn't require my gentlemen caller to have a key card to get to my room door meant it wasn't exactly fancy, but I got more than a bed and a desk, so that was a step up for sure. Mainly I wanted to be comfortable - I was hardly planning to leave the room after all.

In my wildest fantasy, I imagined myself messaging a dozen guys and telling them all to come over. I could picture myself lying there with a huge cock in my mouth, another in my ass, as another guy with a gym fit body and pornstar cock came through the door ready to use me the second either of the others was done. Hell, I have two hands - I could jerk a guy off with each, four at a time. My heart raced at the though of it, and my own cock bulged out of my panties. To lie there exhausted as I was filled with the cum of so many men, losing track of how many had even been and gone.

But that was just a fantasy. I did, and do, reserve that for something I imagine when I wish I could switch place with the tiny girls in the porn videos taking countless dicks the size of their arm, or as something I talk to men about knowing what a filthy slut they'll call me, and how much it'll turn me on to share such a fantasy. In reality, I knew to dream smaller.

As a result, my actual plan was to first invite round a seemingly amazing guy I'd been talking to on Grindr on the Friday night. I'd only been talking to him for a few days, but he was an expert at making me beg for him to fuck me. He had made it clear that he was dominant and damn experienced at it, sending me videos of himself fucking girls and sissies alike, and I kept re-watching videos of his gorgeous cock sliding in and out of their holes and feeling my own ache. It was clear he'd prefer me to come to his house, but I was reluctant - it felt too risky to show up to some stranger's house, and I both was too self conscious to meet him at his door not dressed up girly, and totally averse to the idea of going out in public dressed like a girl. I was relieved and thrilled when he told me he was up for coming to my hotel room - he told me he'd be there at 9, and to make sure I was wearing more than just lingerie. He wanted me dressed up presentably: the slutty stuff should come out later he said. A quick online shopping trip done and I had an outfit that wasn't just lingerie or a costume. And I was on to arranging plans for Saturday.

I knew more than one guy in a night would be a little much for now, but that didn't mean I couldn't have more fun. I worried I might be too sore from Friday to meet anyone on Saturday, so decided I'd leave it open-ended - let someone know I'd be up for some potential fun, but that it wasn't guaranteed. I started off by messaging someone I'd been dying to meet with - a gorgeous black guy with a cock straight out of my dreams, and a body-builder's physique. He was also married, which presented me with the admittedly exciting opportunity to be his dirty little secret, but also sadly meant he told me he wasn't free Saturday. I swapped numbers with him, my first time doing so, with the promise we'd meet soon.

Moving past him for now, I ended up messaging someone who struck me as a very different type of man than Friday's date - whereas the first had been eager to discuss my fantasies and experiences, and tantalise me with suggestions of what we might get up to, Saturday's potential date was straight to the point. His body wasn't amazing, but his cock looked massive - 8.5 inches he told me. He was very clear on what he wanted: to use me to get off. It was shockingly attractive how clearly he had no interest in anything but using my mouth and ass, no attempt to flatter me, other than to tell me I had an ass perfect for being used. I couldn't help but agree.

I'd talked to plenty of guys like this who'd quickly lost me - some had outright said they wanted to **** me, others had just said they would fuck me until I begged them to stop then keep going anyway. I was still nervous and new to this, and while I knew it might be just talk I didn't want to chance it. I had been trying to only arrange to meet guys who seemed respectful as well as dominant, but this guy wasn't exactly that. Still, he expertly toed the line between making me feel like a worthless whore about to be used, and not in any real danger, which was really my sweet spot for being insanely turned on. I told him I might have a hotel room on Saturday night, and he just told me to send him the location and room number and he'd be there. I didn't know which night I was more excited for.

-

The wait until Friday was agonizing, but it finally came around and I left and checked into the hotel room as soon as I could. With me I took everything I'd bought for Friday, and a whole host of other things - lingerie, costumes, heels, toys, lubes. If it fit in my backpack I brought it along. I soon had everything hanging or folded in the wardrobe, and was stood in front of the mirror wearing nothing but a wig and a plug in my ass, trying on everything I had on hand. I sent pictures to both guys - Friday's date, William, sent me requests for pictures he wanted to see of me, and I happily obliged. Saturday's potential date, David, just asked "I thought it was tomorrow you might have a hotel?" I explained I was staying two nights, and meeting someone else the night before. "I'll be there Saturday morning then."

That I had not expected, but I didn't argue. I guess it was no longer a potential meet - impusively I texted him the address and room number, no thought for what I'd do if I didn't feel up to meeting in the morning. I wasn't yet that great at planning ahead - I hadn't actually thought about what I would do on Saturday before evening rolled around, but I guess now I knew. Meanwhile all I could do was watch the time tick by before William would be here. I busied myself by going out to get some wine, and drinking a few glasses in preparation, alongside my usual routine of cleaning and warming up my ass with toys. Despite the wine I still felt butterflies as I put on my outfit ready to greet him - I had opted for a lacy black dress, which to get as tight as I wanted it meant it was pretty short on me. If I bent over my whole ass would no doubt be on display. Easy access. Underneath it though I wore a pair of lacy panties, and sheer black pantyhose. As before, red lipstick, a black lace mask, and my brunette wig completed the look, along with a pair of heels. I had been aiming for something a little classy, but with the length I still looked very slutty. I definitely didn't mind, and highly doubted he would either.

William messaged first to let me know he was on his way, then that he was outside the building, then walking to my room. I sat perched on the edge of the bed watching the shadows underneath the door as he walked up to it, but still jumped when he knocked. I took a glimpse through the peephole - he was older than I usually looked for, probably forty of so, but handsome, square jawed, with only a hint of grey at his temples. I opened the door, stomach in knots.

He stepped inside, greeting me with a smile and a wave of his hand revealing the wine bottle grasped in it. I awkwardly moved to grab an extra mug for him, the only drinkware in the room, and he poured us both a glass worth. My wine knowledge stopped at "it was rosé", but it was fruity and dry. I wasn't really used to talking about being a sissy in person, but he was interested. Thankfully I'd booked a room with a sofa bed and a chair, so we could properly sit and talk rather than rest on the bed. He asked about my first time dressing, my first time using a dildo, my first time meeting another guy. I was bright red as I answered, not reluctant to talk about it but self conscious nonetheless.

"Are you a pretty anxious person usually?" he asked. I just nodded.

"Well I'll tell you exactly what to do, take some of that anxiety away." He stood up, and I quickly necked back my last half mug of wine. I expected him to gesture me over to suck his cock, but instead he walked over to the wardrobe. He rifled through, and placed some things down on the bed.

"Do you want me to change?" I asked.

"Later on." He pointed to the foot of the bed, "Come here and bend yourself over." I did as told.

I felt the fabric of the skirt ride up as I knew it would, exposing my pantyhose-clad ass, no doubt showing the line of my thong between my cheeks underneath. I waited, expecting to feel his hands move up to stroke it, or spank it. A moment passed, and was just about to ask him if something was wrong when I saw him come into view beside me. In his hand, retrieved from the wardrobe, was my buttplug.

"Pull up your dress." Without hesitation I slid the fabric up to my midriff, and quickly felt fingers slide underneath the hem of my pantyhose, pulling them down and exposing my bare ass. They were quickly followed by fingers pulling my thong aside, and then the cool sensation of lube touching my hole had me shiver briefly, before relaxing myself and allowing him to slide my plug into me. I felt it push fully inside until it was held in place, and quickly his hands were back to pull my thong back into place, and slide my pantyhose back up.

"You can stand up now." I did, and adjusted the dress which now left me so exposed.

"On your knees." I knew what was to happen now. He had come dressed in simply jeans and a button down shirt, and he made no motion to remove either.

"Unbutton my belt." I fumbled, never having removed a belt from this angle, but did so.

"Now put those pretty red lips to work."

I quickly had my hands on his jeans, pulling them down to reveal loose fitting boxers clearly showing the shape of a hardening cock. I slid those down as well and before me I saw the second cock I'd seen in person. I took it in my hands before quickly running my tongue along the edge, feeling the soft bulge of a vein and the increasing firmness of it pressing against my hands. I ran the tip of my tongue across the pink head, watching the twitch of it reacting to my slight touch. My mouth was already watering.

I opened my lips, as I had practised so many times on my dildo, pulling my lips back slightly to ensure I didn't touch my teeth against his shaft. His hands reached to the back of my head and held me in place as he thrust inside my mouth, his cock sliding slowly over my tongue and pushing against the back of my throat, making me fight against my impulse to gag. His rhythm was slow but he was firm, forcing me to sit there and take him inside my mouth, no freedom to set my own pace. I could still feel the plug in my ass, and I fought the urge to smile as well as gag.

After a few minutes he pulled out of my mouth, and still gripping my head tightly slapped the head of his cock against my lips.

"You like this cock sissy?" I nodded, eyes wide looking up at him.

"Tell me."

"I love your cock daddy." He hadn't told me to call him that, and I hadn't thought to do so, but it felt right in the moment. He clearly agreed. His hand released from my head and he smiled, pulling me to my feet.

He gestured to what he'd laid out on the back: "Take those and change for me." I just nodded, snatched up the pile and walked falteringly into the bathroom - I still hadn't gotten used to walking in heels right after standing up.

Behind me I shut the bathroom door, and with arms rested against the sink looked at myself in the mirror. I wiped off smudged lipstick with a makeup wipe and reapplied it, puckering my lips and smiled knowing they'd just had a cock between them. A cock only ten feet away from me, on the other side of a door.

I unzipped and dropped my dress, removing my heels and pulling down pantyhose and panties in one motion. His selected outfit for me rested on the edge of the bathtub: grey over the knee socks, a black mini skirt I hadn't realised was only 6 inches long when I ordered it, and a grey marl halter top with a pretty plunging neckline. No panties. I dressed myself quickly, but took a moment to admire myself in the mirror as I adjusted the socks to sit as high as I could. If I thought I looked slutty before, now I looked ready to walk a street corner. My little cock almost showed itself pressing hard out of the front of the skirt as I opened the door back to the bedroom.

Lounged back on the bed, now undressed and looking perfectly comfortable and relaxed, was William. His cock was rock hard and he stroked it as I walked towards him. He opened his legs and beckoned for me to climb onto the bed too. I did so, climbing up on all fours and edging towards his cock still slick with my spit. He let go of it, locking his hands together behind his head as he laid there before me.

"Show me how much you love that cock." I did that the best way I knew how, lying flat on my stomach to give him a view of my round ass peeking out from under the skirt, propped up on my elbows and taking his cock in one hand as I worked my way from the top of his shaft to the base, planting kisses along the length of it before moving back up to take the head between my red lips. I sucked on it, flicking my tongue back and forth across the head, and hearing him faintly moan from in front of me. Emboldened, I placed my hand flat against him, shaft held up between my thumb and forefinger, and began to bob my head up and down as I took his member deeper into my mouth. My other hand moved to his balls, unsure what to do but cup and massage them as my head ducked up and down, taking him just as far to my throat as I could without gagging.

"Take it deeper baby," he said, clearly sensing my careful hesitance. I did as he said, pushing him deeper down my throat, spluttering as I did so. I didn't manage to take it all, but I took as much as I could before coming up for air and to gag slightly. He reached his hand down and stroked my cheek, before softly slapping it.

"Do you daddy to fuck you?" I nodded quickly. He gripped my chin in his hand, his fingers strong and warm against my skin.

"Beg me."

"Please fuck me daddy." He ran his thumb across my lips, and I instinctively moved to suck it.

"Good girl..." he pulled his thumb out of my mouth, and slid himself off the bed, moving to position himself behind me. I lay there flat against the bed and felt him grip my waist and swiftly drag me back, my legs falling to the floor leaving me pressed in the same position I had been in when he plugged my ass. I knew what was coming as he gripped it and gently removed it, rubbing a finger against my hole but not pushing it inside.

He headed over the bedside table and grabbed a condom, and I watched as to my left he tore the wrapper off and ran the condom down his shaft. He pumped a few squirts of lube into the palm of his hand and ran it along the length of it, before grabbing the bottle and walking up behind me and out of my line of sight.

"Get on the bed, on all fours." I did so, feeling my own hard penis flopping in front of me. The bed shifted as he climbed up on it himself, placing one hand on my ass cheek as the other, slick with lube, pushed a finger into my ass. It pulled out, and I felt something bigger push up against me.

"Beg daddy for this cock." I didn't hesitate.

"Please daddy, I need your cock so bad."

His head pushed inside of me, and I felt that increasingly familiar mix of discomfort and pleasure as he pushed deeper in. I could feel myself stretching to take him, and resisted the urge to bury my face in the bed - he'd told me he wanted me on all fours, and that was what he'd get. Again his rhythm was slow, gentle but firm, as he slid back and forth inside of me, reaching one hand the grip the fabric of the back of my halter top, the other gripping my waist.

Without warning he picked up the speed - I gasped as I felt him slam deeper inside me, but after a few thrusts, just as I was getting used to the more aggressive pacing, he slowed down again. A minute of slow fucking, a few seconds quick, a minute slow, a few seconds quick. Each time I wished he'd keep going faster - I'd gotten used to the feeling of his cock, and now the feeling of being stretched out was far more pleasure than pain.

A good amount of time passed before I felt him pull out of me. I had thought he was just going to lube his cock again, but instead he grabbed my waist and pulled me back off the bed, slapping my ass as my feet fell to the floor again. I was ready to bend over the bed but instead he told me to stand up, and made his way over to the sofa. He sat down, pumped a couple of squirts of lube onto his wrapped cock, and beckoned me over again. I walked towards him, and he sat up, grabbed my waist and guided me to spin around, my ass facing him.

"Now you're going to sit on this cock." I said nothing and let his hands guide me back towards him, leading my ass down with one hand as I felt his dick press up against my hole again, sliding across it. It took a moment, but he guided it into me, pressing inside of my ass as I stood, squatted, before him. I'd never riden a cock or a dildo, and the feeling wasn't the most comfortable - my legs ached as I kept myself perched upon his cock, and I took a moment to steady myself. No doubt sensing this, his hands both came up to grab my waist and lower me down onto his shaft, setting the pace for me.

I let him guide me up and down, feeling his cock pressing into me, less comfortable than before, but I caught sight of myself in the mirror opposite me - my wig was slightly crooked, and one sock had already fell down slightly below the knee as they always inevitably did, but it was like watching a scene from a porn playing out in front of me, a barely dressed girl bobbing up and down on a huge cock. I grinned, before quickly dropping the smile as I found myself moaning as the pace of thrusts gradually increased.

I feared my legs would give out under me, feeling them trembling, and William pushed me upwards, his cock sliding out of me and leaving me aching for more. He quickly gave it, his hand shoving my stomach backwards and sending my falling onto the bed. Wordlessly, he grabbed my legs and raised them up above his shoulders, leaving me flat on my back as he stood before the bed's edge, lining himself up with my hole that cried out for his cock again.

"Have you ever ridden a cock Alice?"

"No daddy."

"Have you ever been fucked like this?"

"No daddy."

"Would you like to be?"

"God yes daddy."

He thrust inside me in one fluid motion, forcing me to cry out in shock. A hand rose to my face and covered my mouth as he began to push himself deep inside me, the deepest he'd gone yet. I could feel him pressing up inside me and moaned into his hand, my head lolling back and my eyes unfocused as all I could do was enjoy the overwhelming feeling of him filling up my asshole.

"You're taking it so well sissy." I could only moan in response, biting my lip to stop from crying out.

I lost track of the time he spent inside me before abruptly pulling out. I looked up in surprise and confusion as he dropped my legs down from his shoulders, and climbed up onto the bed straddling my chest.

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.