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My First Sissy, Chapter 4

"Josie comes to meet me in a hotel, and we finally give each other what we need"

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Over the next week, every single morning that I went into class, the only thing I could think about all day was getting home, locking my bedroom door, and video-calling Josie. Each night, she would show off a different outfit for me and tell me how badly she needed me inside her as I watched her fuck her little hole with the dildo I’d bought her.

I’d tell her how to play with herself, how fast to go, how deep to go, and what position I wanted her in, and she would dutifully comply with my every command, sliding her toy in and out of her tight ass until her little clitty exploded in her panties. On the third day, I forbade her from touching her clitty at all, instructing her that she was now only allowed to cum from the sensation of the new toy inside her.

By the fourth day, she could take the full eight inches of fake cock inside her, all the way to the hilt. I watched as she slammed herself down its full length, fake balls slapping against her perfectly-round cheeks, arching her back in pleasure as she moaned my name.

On the fifth day, I made her stay completely still with the whole length of the dildo inside her, as I stroked my cock on the screen. She would try and grind and shift her weight down onto the toy buried in her ass, and I would command her to stop. She whined and begged, and I could see the bulge of her clitty straining against her panties, but I refused to let her fuck herself properly.

“Good girls wait for Daddy to cum first, little slut,” I said as I stroked my cock slowly, “You’ll have to find a way to make Daddy cum if you want to be able to play with your little bio-cunt properly.”

My denial of her pleasure seemed to turn her on even more, and she moaned involuntarily and shook uncontrollably as she ran her hands over her body and told me that I owned it, how badly she wanted my hands, my lips, and my cum all over her. I listened as my gorgeous, little slut, dressed in a little blue sailor’s outfit, talked dirty to me, telling me about all the things that she wanted me to do to her. I came hard as she described how she wanted to be used on camera by me, begging to be bred in front of strangers watching on the internet as I filled her with my seed.

After I had cum, I gave her permission to do the same, and she fucked herself even more wildly than she had done on any of the nights before, screaming loudly as her clitty sprayed over her bed sheets, before collapsing onto the bed where she continued to whimper as aftershocks of pleasure rolled over her.

“I think you’re ready, princess,” I told her after she had stopped shuddering from her last overpowering orgasm.

“For what, Daddy?” She asked, still panting.

“To come and take a real cock in that perfect little ass, baby,” I replied.

That statement made her moan loudly and her eyes rolled back as she quivered again.

“When, Daddyyyy?!” She whined.

“This weekend, little slut. Daddy has already booked the hotel room that you’re going to come meet him.” I replied

Josie had started to touch her clitty through her soaking panties at the thought of this.

“No touching that pretty clit, princess,” I commanded, “remember that Daddy owns it now.”

I couldn’t sleep that night, too turned on to even close my eyes, the thought of what was to come tomorrow making my cock ache. After the first night I had watched Josie cum with her dildo buried inside her, I went online and booked a hotel room. My hands had been shaking in anticipation as I confirmed the booking, and I had been struggling to keep the surprise from Josie all week.

I had booked us a double room in a budget hotel in a city halfway between us. Even though I was sure we wouldn’t be leaving our room all weekend, I wanted to make sure we wouldn’t be spotted by anyone we knew. As I selected a room with a king-sized bed; my mind conjured images of Josie, looking irresistibly sexy in her lingerie, lying back across it and begging me to come and get on top of her.

From early on in our relationship, just to ensure that we had a little space from each other every now and then, Katie and I had made a rule that we would spend at least one weekend a month apart. I had already told her that I was going away on a weekend with a couple of friends from back home who I hadn’t seen in a while. Even as I told her this lie, my cock started to strain against my boxers, thinking about how I was really going to spend the weekend fucking her brother senseless.

The Friday evening after lectures, I made the hour-long drive to the hotel I had booked for me and Josie. My cock was throbbing in my jeans the entire way as I thought about the weekend ahead. I had told Josie to pack her favourite outfits, lube, and the dildo I had bought her. Even though this was a huge step for both of us, I had no doubt she would come. The video calls and text messages we had been sending each other had made our desire for each other so intense, that there was only one way for it to be satisfied.

Although I had actually only seen Josie, Joe’s sissy self, in the flesh twice, she had been sending me pictures of her body every night for the last month, and I had been stroking my cock on camera while she fucked her little hole for me all week. I already felt like I knew every curve of her feminine body, every inch of that perfect pale skin. It helped that the second time I’d ever seen her, dolled up and wearing a slutty schoolgirl outfit, I’d watched her gobble my cock before she had swallowed every last drop of my cum.

I checked into the hotel, left a package with the hotel receptionist, and went up to our room to await Josie’s arrival. The room was perfect. It was the last room on the corridor, around a short corner and out of sight of the main hallway. Inside there was a king-sized bed with fresh white sheets, a small desk and chair below a window that overlooked the street, six stories below, and a small bathroom with a walk-in shower that was big enough for two. It looked like it had been designed specifically for how I intended to use it, a weekend of sex.  

As I settled onto the bed, my phone vibrated in my pocket, instantly making my heart race. The message was from Joe.

“I’m downstairs, Daddy. What room am I coming to?” the message read.

My cock was instantly hard in my jeans at the thought that Joe was so close, having travelled over an hour to a cheap hotel in an unfamiliar city, for the sole purpose of having my dick inside him. He didn’t drive and had been uncomfortable travelling on the train as Josie, so I had made certain plans for his arrival.

“I’m glad you made it, princess,” I wrote back, “go to the receptionist. There’s a package waiting for you.”

My hands were trembling as I sent the message, the sense of anticipation was almost too much to bear.

“Inside, there is something that you need to put on for me,” I continued, “I want you to go to the disabled toilet, just around the corner from reception, get your make-up on for Daddy, and wear the outfit he has been generous enough to buy you.”

I waited a few seconds, breathing hard as I awaited Joe’s reply.

“Yes, Daddy,” came the simple response.

I sat back on the bed, my solid cock aching so bad now that I had to force myself not to take it out and start stroking it as I thought of what I had left downstairs for Joe. The package I’d left at the reception contained a black strappy lingerie set that would expose Josie’s little tits, hips, and ass fully. There were no panties, just straps that looped around the thighs and stomach. The open-cup bra looped up to the neck and was connected to a collar, which had a metal ring made for a leash. The leash I was now holding.

Joe had bought himself a pair of black high heels, and I had made him bring them to the hotel and I told him to put them on too. Although the thought of exposing him in public turned me on more than I thought possible, I knew that there was no way that he would be able to walk through the hotel dressed like that, so I had packed a beige trench coat in with the lingerie. The trench coat stopped at thigh level, and, although Joe would be spared from walking through the hotel in nothing but a few black straps and a pair of high heels, he would still look like a slut who had travelled to a hotel to be fucked.

I was pacing the room, struggling to contain my excitement, when there was a knock at the hotel door. I strode over and opened it, and my heart skipped a beat. Josie stood in the hallway, the brown hair that flowed over her shoulders had been slightly curled, and her eyes were lined with heavy mascara. Her cheeks were rouged, and her lips were covered in bright pink lipstick that made them shine.

The trench coat was wrapped tight around her, but it finished at her upper thigh, exposing her long smooth legs. Even though she was wearing four-inch, strappy high-heeled shoes, she was still a good six inches shorter than me. She stood under the soft light of the hallway and looked up at me with her big blue eyes and realised I had never seen anyone as sexy in my whole life.

“Hello, Daddy,” she said, her voice quivering.

“Hello, princess,” I replied, struggling to keep my own voice level.

“Can I come in, Daddy?” she said, looking up pleadingly.

I couldn’t take my eyes off her, she looked so fucking hot, I needed her then, more than I had ever needed anything in my entire life, but I wanted to take this slow, to savour every single second.

“Open your coat, princess,” I commanded.

“Out here, Daddy?” Josie asked uncertainly, looking around.

“Yes, little slut.” I replied as I stared down at her.

She looked hesitant for a second, and then unbuttoned her trench coat and held it open, revealing the lingerie underneath. I let out an involuntary groan as I took her in. The lingerie looked better on her than it had on the model on the website. The black straps hugged her body and accentuated her slender feminine frame, the collar was tight around her neck, the metal ring protruding towards me. Her clitty was exposed, already hard and leaking a little.

“Fuck me, you’re so sexy,” I whispered.

Even under her makeup, I could see Josie blush at this compliment.

“Get on your knees, baby,” I instructed.

Josie’s eyes widened in surprise, and she looked around her before looking back at me.

“Now, Daddy?!” she asked.

“That’s what Daddy said, princess,” I replied firmly.

Josie slowly got to her knees as I unbuckled my jeans. She reached out and undid the buttons with shaking hands, opening my jeans and sliding them down. I wasn’t wearing any boxers and my aching cock sprang out of my jeans as she pulled them down. She gasped and looked up at it hungrily. She reached up and encircled my rock-hard dick in her hands before sliding them up and down my shaft.

“Fuckkkkk, I’ve needed this so bad,” she said in an eager, girly voice, looking up at me longingly.

I lifted her chin a little and fastened the clasp of the leash I was holding to the collar around her neck. She whimpered in anticipation as I did and continued to stroke my cock slowly. I stood upright and pulled on the leash firmly and he knelt up a little and kissed the tip of my cock, then planted more kisses all over my shaft and shaved balls. I pulled the leash tighter, and she opened her mouth and slid her lips around my cock.

She had been practicing with the dildo, and I watched as her mouth glided down every inch of my dick, until my shaft had disappeared completely between her lips and her nose was resting against my stomach. The last time she had sucked my cock, it had been the best blowjob of my life, this time was even better.

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I increased the tension on the leash and she reached around and put her hands on my ass so that she could force my hips forward and drive my cock even further into her throat. She stayed there, looking up at me, eyes watering, her saliva running down her chin and onto my balls, before I released the leash a little and she popped her head back and gasped for air.

Just a few minutes ago, before lowering herself to her knees, she had been checking the corridor to ensure it was clear before unfastening her coat. Now it was obvious that any concern about getting caught was outweighed by her urgent need to devour my dick. She slid her mouth up and down my cock, moaning and slurping loudly as she soaked my shaft in spit and pre-cum, encouraged every now to take me even deeper by a little tug on the leash I held.

The last time she had my cock between her lips, I held her head steady as I fucked her mouth, grinding my hips to make her take me as far down her throat as she could. This time I didn’t need to touch her. She was using my cock to fuck her drooling mouth all by herself, eagerly bobbing her head up and down my entire length in a bid to please her master, copying the little sluts she had been watching online. I didn’t really need to use the leash I held at all, but she looked so sexy with it trailing from the collar around her neck into my hand.

Her trench coat was open, and I could see that her little clitty was rock-hard and leaking constantly now. A combination of pre-cum and spit leaked down her chin and dripped onto the tip, making it even wetter. I knew she was desperate to reach down and touch it, but she understood that that was forbidden unless I gave the word to allow it.

Many times over the last month, as we had been sex-chatting on the phone, Josie and I had watched porn together on the internet, talking about how we would re-enact the videos we shared. As I looked down at her, kneeling in the middle of a hotel corridor, her perfect body wrapped in strappy black lingerie, taking my cock between her glossy pink lips, I felt like I was living a far hotter scene than any I had ever watched online.

“Fuck, baby, you’re going to make Daddy cum!” I moaned as she started bobbing her head up and down my dick even faster.

She gripped my ass hard and pulled me into her one last time, looking up at me as she moaned something unintelligible onto my shaft, her voice causing vibrations down the length of my cock. I pulled the leash tight as my cock exploded in her mouth, bucking my hips as waves of pleasure hit me, so powerful they almost made my legs buckle. She held me in her mouth until she felt my orgasm subside, and then I watched, my cock still buried in her throat, as she swallowed every drop of my cum.

She knelt back and the length of my cock slid from between her lips. Unbelievably, I was still hard. I needed more of her. Lots more. I used the leash to drag her to her feet and pulled her into the room, kissing her passionately as I stripped off her trench coat. She kissed me feverishly, forcing her tongue into my mouth. I sucked on it, tasting my own cum as I did. My hands hungrily groped every inch of her perfect body, running down her back, down further, onto her perfectly smooth ass. I squeezed it and pulled her into me, grinding my hard cock against her leaking clitty.

Josie was panting hard as we kissed, her arms locked around my neck as she rubbed her clitty desperately against my shaft, trying to get herself off on it. I cupped my hands under her ass and lifted her effortlessly off the ground. She immediately wrapped her legs around my back, her face just above me now, cupping mine as she continued to kiss me hungrily. She wasn’t wearing any panties, so there was nothing to pull aside as I angled her hips up and pushed the tip of my rock-hard cock against her naked ass.

“Oh, Godddd!!!” she gasped as I pulled her cheeks apart, the head of my cock pressing against the opening of her tight little hole. My dick was already soaking from a mix of cum and Josie’s spit and it slid easily inside her as I lowered her onto me.

“Oh fuck, babygurl,” I moaned softly as I felt her ass envelope the head of my throbbing cock.

She gasped again and broke off from kissing me to look into my eyes as I let her drop slowly down the length of my shaft. Her face was almost touching mine, and I stared into her eyes and listened to her whimper in pleasure as my cock slid slowly into her, inch by inch, until it was buried inside her ass, all the way to the hilt.

I kissed her fanatically as I carried her over to the bed, fighting the urge to cum again just listening to the little groans she made as my cock moved inside her with each step. I laid her slowly back on the bed and looked down at her. Her eyes were half closed in ecstasy and she was biting down on her lip, the thin straps of the black lingerie accentuated the flawless curves of her body and made her look completely feminine. Only her clitty, rock-hard, and leaking pre-cum all over her perfectly flat stomach, hinted at the fact that this unbelievably gorgeous girl lying beneath me wasn’t entirely female. She was the sexiest thing I had seen in my entire life.

Standing at the edge of the bed, Josie lying with her back against the sheets, her legs still locked tightly around me, I started to slide my cock in and out of her. She arched her back and started panting hard with each thrust as I pulled my cock back, nearly sliding it out of her, before moving my hips forward to drive my entire length inside her again. I ground my cock into her and she whimpered as she strained to use her legs to pull me deeper with each thrust.

I moved my hands over her body, down the sides of her stomach to the curves of her hips, holding them to pull her onto me with each thrust. I couldn’t help myself, I needed to have my hands over every part of her. As I drove my cock into her again, I reached one hand up from her hip and wrapped it around her perfect little clitty.

Josie squealed and opened her eyes suddenly as she felt my hand stroke her clit. She must have been barely hanging on. Without warning, she cried out and arched her back. Her clitty exploded in my hand, showering cum over her stomach and chest. She shuddered as she came, each convulsion forcing her ass back onto my shaft even further and making her scream out again as another pulse of pleasure rocked through her. Her orgasm seemed to last forever, and every time I slammed into her, more cum leaked from her clitty to cover her flat tummy and trickle down the sides of her stomach onto the bed beneath her.

If she hadn’t made me cum in her mouth minutes before, the sight of her bucking and moaning on the end of my cock as she climaxed would have sent me over the edge too. I kept fucking her until the convulsions of her orgasm subsided and she collapsed back onto the bed, panting and still shaking occasionally in the aftershocks.

“I’m sorry, Daddy”, she said, looking up at me when she could finally catch her breath, “when you touched my clitty I couldn’t help myself.”

“Such a naughty girl,” I growled playfully, “now Daddy’s going to have to teach you a lesson.”

I leaned over and started kissing her again, slowly sliding my rock-hard cock in and out of her boi-cunt.

“Oh God yesss, teach your little slut a lesson,” she murmured as she ran her hands down my naked back to rest on my ass, pulling me into her every time I ground my hips forward.

I reached behind me and unlocked her legs from my back, lifting them up until they were resting on my shoulders. Josie was folded in half, and from this angle, I could push my cock even further inside her body. Her slender body was lithe and flexible and bent over in this position, her clitty was only inches from her face.

I began rhythmically sliding my cock in and out of her, starting slow before building up faster, until I was slamming my cock into her so hard and fast that my balls slapped against her hole every time I thrust forward, and she rocked back on the bed. Her hands were on my ass, still pulling me into her, squealing loudly every time I bottomed out in her hole.

“Do you like that, my little whore?” I panted as I hammered into her again.

“Yes, Daddy!!!” she whimpered back, “I fucking LOVE it!”

“What do you love little slut?” I demanded as I sped up.

“I love your cock, Daddyyy!” she cried out, “I love it!! I NEED it in me.”

All the weeks of pent-up lust for her, the nights where my cock was so hard for her it hurt, were now finally being realised as I pounded into her, fucking her harder and faster with each thrust. I looked deep into her eyes as my dick plunged home, listening to her beg for more.

“Louder, princess,” I said as I sped up, slamming into her as she threw her head back and started to moan continuously, “I want our neighbours to hear you.”

“I NEED YOUR COCK DADDYYY!!!!” she screamed, so loud that I was sure they would hear her all the way down the hall, “NEVER STOP FUCKING ME DADDYYY!!! NEVER STOP FUCKING YOUR FILTHY, LITTLE WHORE!!!!”

With that she squealed as another orgasm rocked through her body, her clitty spraying cum over her face, lacing her cheeks and mouth. She closed her eyes and pulled me into her as she cried out, her clitty jerking and spurting more cum onto her face and chest. The sight of her cumming all over herself was too much for me. I grunted and thrust into her again as I climaxed, my cock gushing cum into her cunt. I leaned down and kissed her as wave after wave of pleasure swept over me, continuing to slam my dick into her as I emptied my balls deep inside the tight hole that engulfed my shaft.

“Oh God, I can feel it, Daddy!” she cried out as my seed filled her, “I can feel your cum in me!!”

It felt like my orgasm would never stop, and I buried my cock deep into her and held it there as I felt it pulse and throb against the walls of her ass, emptying more cum into her with each spasm of my shaft. Finally, just when it felt like I was on the verge of passing out from pleasure, my cock stopped twitching inside her. She pulled me down and kissed me feverishly and as I pulled my rigid cock, satiated for the moment, out of her. I could feel my cum trickle out of her ass, onto the tip of my dick as I pulled out.

I collapsed on the bed beside her, breathless. She rolled on top of me and wrapped her legs around mine, continuing to kiss me hungrily. I could feel the slick wetness of the cum that coated her body, against my skin, covering us both as we ground against each other. She rubbed her clitty against my cock, both of them wet and still partly hard. Even though I had just completely emptied my balls inside her mouth and ass, I could feel myself getting turned on again.

“Did that beat fucking your dildo?” I said, grinning as she kissed my neck and rubbed her body against mine.

“Oh God yesss, that beats everything,” she replied breathlessly and then smiled naughtily, “did it beat fucking my sister?”

I grinned and then rolled her under me, looking down at her stunning face and perfect, slender body.

“Mmm,” I mused teasingly as I kissed her lips, “it did princess, but I’ll have to fuck you again to be absolutely sure.”

“I don’t think one more time would be enough,” she said as she locked her legs around my back and reached her hands down to wrap them around my rapidly hardening dick, “Luckily you have an entire weekend to fuck me and make sure.”

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Written by michaeldelangel
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