A Sissy Slut's Diary Ch. 01

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.