A Sissy Slut's Diary Ch. 02

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 rape 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.