I started crossdressing when I was younger, around the age of sixteen or seventeen, and it started with the usual story of borrowing my mother's underwear when she wasn't around. Unfortunately, this wasn't sexy enough for me and seeing as I didn't have a sister to borrow from, I ended up buying my own knickers. Fast forward to being twenty-eight, still never been with a man, but constantly thinking about it.

As I got older, this was able to expand, and I was able to drive to buy more things and toys. Unfortunately, I've never managed to meet anyone due to nerves and some bad timing. But this story is based on the fantasy I've had for a long time. I hope you enjoy it, and comments and feedback are appreciated, and I would be willing to work on more stories. I've labelled it as chapter one just in case anyone wants me to write more.

I'd joined many different dating sites over the years, and swingers’ sites in the hopes of finding people who'd be interested in what I had to offer. I'd joined these sites under the name Alexis, obviously to remain discrete in case I encountered anyone I knew. I'd set up my profile to include my three main fantasies; dressing up for a guy, joining a M/F couple to make a bisexual threesome and the third one was to join a M/F couple where I get pegged by the wife and fucked by the husband. It finally seemed like I'd found the right guy for fantasy number one.

He lived far enough away from me where I could be discreet but once again, bad timing struck, and the full country was in lockdown. We continued to message throughout the lockdown with the promise that we'd meet once it was all over. Amidst all this, I have a girlfriend. She just wouldn't understand what I'm going through. The dream is one day that we can share a cock and she'll watch me get fucked by another guy.

Finally, the lockdown was over, and we could go ahead with the meet. In preparation, I'd bought some new lingerie and ladies' clothing that I could take with me. I got up nice and early on the morning of the meet, jumped in the shower and shaved my entire body so I was nice and smooth for the meet. I packed my clothes that I was taking with me into a small bag and laid out my outfit for the drive. I slipped on my lace knickers and pulled on a pair of stockings before putting a t-shirt and a pair of jeans to hide the sissy beneath. Getting everything together, I was trying my hardest to make sure I didn't flash my parents a hint of lace before heading out.

After about an hour’s car journey, I arrived at the house of the older gentleman who was about to take my virginity. I grabbed my bag out of the car and headed to the door. He answered not long after I knocked, and this is where I saw him for the first time. He was around 6' 2" and was around fifty-five, but he could have passed for forty. He was fit for his age and told me to prepare for a long day.

After entering his house, he pointed me in the direction of the living room while he locked the door and collected us a drink from the kitchen. We sat and chatted for what seemed like forever, while my eyes kept wandering to his crotch, wondering what awaited me underneath those jeans. After a good catch up, he started to move closer to me on the sofa. He leaned over and started to rub my inner thigh while telling me he was disappointed that I hadn't turned up dressed up for him.

'Be patient, Daddy, the time will come,' I told him.

Nerves started to rise within me, I didn't know what to do. I'd never been with a man and I feared disappointing him. I tried to keep the conversation going to prevent the inevitable, but that's when his hand reached my crotch and he started rubbing my cock through my jeans. With the first contact, I let out an audible gasp or a moan and at this point, he took his opportunity.

He leaned in to kiss me, pressing his lips against mine whilst tightening his grip on my cock, which was now growing at a rapid pace. Suddenly, as his tongue entered my mouth for the first time, any nerves I had were now gone and I felt like I was floating on air. Everything felt so good, and he was taking control just like I wanted him to. I needed him to guide me!

I was brought back to reality when I felt him move my hand onto his crotch and I felt the length of his cock for the first time. He had me right where he wanted me; I would do anything to please him right now. And that's exactly what I was going to do. As we continued to kiss, I began searching for the button to undo his jeans, and before long I had found it and pulled down his zipper.

I was surprised to find that he wasn't wearing any underwear and I had direct access to his rock-hard cock. It was the first time I'd held another man’s cock and I was mesmerised by it. The feel, the touch, everything. It must have been at least seven and a half inches, if not more.

It was like my body was possessed. I instinctively broke the kiss and slowly dropped to my knees on the floor in front of him. Reaching up, I started to pull his jeans down and he lifted his ass off the sofa to make it easier for me, leaving him sat there with just his t-shirt on. I just stared at this magnificent cock that was just in front of my face, almost forgetting what I wanted to do next. I took hold of the shaft with one hand and began to slowly stroke him up and down whilst staring straight into his eyes.

'You want to suck on it?' he said.

'Yes, please,' I replied almost instantly.

I leaned forward and began to lick just above where his balls sat and slowly teased. I knew what he wanted, and he knew what I wanted. I slowly licked my way all the way up from the base of the shaft right to the tip of his cock. He let out a long, satisfied groan as I did this.

'I love those knickers you've got on by the way,' he said. Little did I know, but as I went to work on his cock, I hadn't realised that my t shirt had ridden up, exposing the pink lace secret I was hiding beneath my jeans.

My confidence slowly started to grow the more he moaned and groaned. And for the first time in my life, I took the head of his cock into my mouth. This was it... I was giving my first ever blowjob. I began to bob my head up and down like there was no tomorrow.

There was no stopping me now. The next thing I had to do was to deepthroat this massive cock, I had to try. I began to lower myself down on his cock. I must have got about halfway before I started to gag.

'Whoa, slow down, Alexis. Take it easy,' he reassured me.

I decided to imagine what I like with my girlfriend and that’s what I went with. I took the top part of his cock in my mouth and began to bob my head up and down while I used my hands to wank him off at the same time. The moans and groans started again; my own dick was straining against the inside of my jeans.

He reached a hand across my back and slowly worked his hand to the inside of my pants and began groping at my cheeks. It felt incredible and he had me even more turned on now, so I increased the pace on the blowjob and the moans from my new Daddy were coming a lot quicker now and the intensity of his breathing was off the charts. I could sense an orgasm building.

'If you... don't... stop... I'm... I'm going to... cum,' he said.

'I want it, Daddy, cum for me.'

I went back to it and less than thirty seconds later, I felt his cock begin to swell in my mouth, then the pulsing of his cock and then I felt the first spurt of cum hit the back of my throat, then the second and finally the third. My first taste of cum (other than my own) and it was amazing. I was hooked and I wanted more. I licked his cock clean and swallowed everything he gave me before standing in front of him. He looked spent.

I slowly removed my t-shirt before turning round and slowly peeling my jeans down my legs, making sure to bend over and give him a good view as I slowly revealed my lace knickers and hold ups. Once I was stripped down, I turned to face him.

'Wait here, Daddy, I need to go and get ready for you.' I quickly got up, collected my bag, and headed off upstairs to the bathroom.

I couldn't get up the stairs quick enough. I couldn't wait any longer. I was about to lose my anal virginity. I quickly stripped out of my lace knickers and put a pink lace thong on. Fishing into the bag, I pulled out the matching lace bralette to go with it, as well as the tight black mini skirt I'd brought and white blouse. I finished the look with a pair of glasses.

I might not have the wig and makeup yet, but I was aiming for a sexy secretary look. It was extremely hard to hide my current state of arousal; there was an obvious bulge in the front of my skirt.

I was ready to head back downstairs, but I was surprised by Daddy when I opened the bathroom door; he stood there, waiting for me. I swear I could have seen his jaw hit the floor... not to blow my own trumpet.

'Do you like?' I asked, giving him a little spin.

'Jesus Christ, come with me,' he said as he approached me, pointing in the direction of the bedroom. As I walked in front of him, I could tell he was checking me out from behind. Then I felt him trying to lift my skirt up so he could get a good look at my ass, I slapped his hand away, telling him he had to wait. I couldn't help but think if this is what a girl felt like when she was about to lose her virginity.

Once in the bedroom, I sat on the bed and took his cock into my mouth once more, trying to get him nice and hard so he could fuck me. After sucking him for a few minutes, he pushed me away and laid me down on my back on the bed, he lifted my skirt, so it was bunched around my waist and then freed my cock from the constraints of lace.

He swallowed my cock in one plunge; I wasn't the biggest by any means, normally around six inches when hard, and a grower not a shower. It felt incredible; it was true, guys knew how to give the best blowjobs. I didn't think it could get any better and then I felt him pull the thong out from in between my cheeks and start slowly rubbing his fingers over my hole.

I could feel an orgasm building, I had to beg him to stop. 'Please, Daddy, please stop, I'm going to cum soon.' He had no intentions of stopping; well not until he had me right on the edge of the most amazing orgasm and then he stopped.

I was panting and breathing extremely heavily. He let my cock slip out of his mouth before picking my legs up and pinning them towards my chest, he then started to use his tongue to get my hole nice and wet. It was a whole new level of pleasure I'd never experienced before. This was the first feminine groan I let out and it wasn't even intentional. I tried to reach for my cock to finish myself off, but he grabbed both my arms and pinned them to my side. I was being dominated and I fucking loved it.

'Please fuck me, Daddy... I want you to pop my fucking cherry.' I was practically shouting at him now; it was too much. I needed to feel him inside me.

He made his way over to his bedside cabinet where he pulled out a bottle of lube and a condom. He flipped me over and told me to get up on all fours. He gave my ass a nice little slap for good measure, which caused me to let out another moan. He opened the lube and let it drizzle down between my cheeks before inserting one of his fingers into my ass, this caused me to lurch forward as it was unexpected. He pulled me back closer and reinserted his finger into me and began to finger fuck me, before shortly adding a second.

'Are you ready, baby? You ready to be fucked?'

I couldn't respond, all I could do was groan under the pressure of his fingers. His fingers withdrew and I heard him opening the wrapper of the condom. I looked over my shoulder and I could see him rolling it down his dick and applying lots of lube. I turned my head again and buried it in the bed sheets, ready for what was about to come. I felt the head of his cock pressed against my ass.

'Right, baby, I'm not going to push it in, I want you to back yourself on to me so you can control it.'

As I began pushing back, I remembered everything I'd read about pushing out to make it easier; there was a sudden jolt of pain. This caused me to cry out in pain.

'Ssshhhh, it's okay. That's just the head going in, you're past the hard part now. Keep going.' He was very reassuring. I gritted my teeth through the pain and continued to push back, and then I felt his hands on my hips and his balls resting against mine. He leant over me and whispered in my ear, 'Now the fun begins.'

He slowly withdrew himself, and I'd never felt so empty. But that feeling didn't last long as he thrust himself back into me causing a loud groan to escape from me. He really started to fuck me now, long, hard thrusts.

I was gripping the bedsheets and loving every second; this was better than I could have imagined! My hard cock was bouncing beneath me as he fucked me. He pulled out and pushed me down on to the bed before putting his legs either side of me and with one easy push, he was back inside me again.

This time there was no letting me get used to him, he was really going to town and pounding away at my hole. Beneath me, with every thrust, my cock was rubbing against the bed sheets and I could feel my orgasm building. I'd always fantasised about cumming without touching myself and it was about to happen. Daddy continued to pound me, there was nothing I could do to prevent my orgasm.

'Daddy... ugh... I'm... ugh... cumming...ahhhhhhh.' That was it; beneath me I felt my cock pulse four or five times, and even though I couldn't see it, I knew I'd never cum that much before.

'Did you just cum all over my bed?' He followed that up with a thunderous spank to my ass.

'Sorry, Daddy, I didn't mean to, it felt so good!' I felt bad, like I'd done something I shouldn't have.

He pulled his cock out my ass and I turned my head to look at him. He had a devilish smile on his face. 'You are a naughty, naughty girl. You're going to clean that up using your tongue.'

He went and sat in the chair in the corner of the room while he watched me get up on my hands and knees and lick the cum clean from the bedsheets. I was no stranger to eating my own cum, so I didn't mind. I turned to face him, and he was sat in the chair, stroking his cock. 'Get over here and sit on my dick.'

I got up from the bed and made my way over to him, taking my skirt off and my shirt, leaving me in just my lingerie. I grabbed the lube and reapplied some to myself and the condom before straddling him and impaling myself on his massive dick. I let out a large moan as I sunk to the bottom of his cock.

He started to kiss me while we fucked, and I'd never felt anything so erotic. I was bouncing up and down on his dick, moaning loudly in between kisses. If his neighbours were home, they knew what we were doing.

He told me he was getting close, then he took over. He gripped me tightly so I couldn't move and then pounded away at my hole. I was going to be sore after this, but once again I was rock hard. Then with one final thrust and a grunt, he filled the condom he was fucking me with.

Absolutely spent, I collapsed on top of him with the biggest smile on my face. He kissed my forehead, and I'd never felt more special. I rolled off him and struggled to make my way over to the bed for a lie down. My legs were like jelly.

After regaining my composure again and a little bit of the feeling had returned in my legs, I made my way to the bathroom, asking if I could use the shower to clean myself off and freshen up. Teasing him once again, I took off my remaining lingerie one item at a time, leaving a trail of stockings, bras, and knickers as I made my way to the shower.

Stepping in, I let the warm water run over my face and then down my back, before the shower curtain flew open and Daddy was stood there, and yet again he was hard. He stepped in and dropped to his knees in front of me, immediately taking my soft cock in his hand and starting to suck me off. Within seconds I was hard, using the wall to support me as my legs still weren't back to normal.

'You want Daddy's cock one last time?' I didn't think I could take anymore, but he was pushing all the right buttons and I couldn't resist.

He turned me around and thrust his cock straight into my awaiting ass, I was very aware he wasn't wearing a condom. We had discussed bareback in our messages and I knew he was clean, but we had no plans to do this. It's true what they say, it feels so much better without a condom, I could feel every part of his dick. The first time he fucked me, there was a hint of love making to it, but this time it was pure lust, he just wanted to come again.

He was seriously fucking me hard now, each thrust almost lifting me off the floor and leaving me on my tippy toes. If this is what it's like to be fucked, then I want this every day. There was a loud slapping noise every time he thrust himself inside me and noises were escaping me that I didn't know were possible.

'Get on your back, I want to see your face when I cum deep in your boi pussy.' This just turned me on even more, I jumped out of the shower and laid a towel down on the floor, and he quickly knelt between my legs before starting to fuck me again - only this time he had his hand wrapped round my cock and was stroking me.

This tipped me over the edge and caused my cock to explode, cum splattering all over my own chest and face. As I came, my ass clamped down around his dick causing him to buck wildly and then I felt the first spurt of cum coating my insides. A massive grunt with one more thrust unloaded more of his seed inside me before he collapsed on top of me, kissing me as we lay next to one another, with his cum leaking from my asshole.

'I'll let you get that shower now.'

We both laughed, and I jumped in the shower to clean myself and try to get the cum from my ass. I collected my things as I made my way back to the bedroom to get dressed, picking up my knickers which were now soaked in cum. Luckily, like every good girl, I'd packed a clean pair of knickers. It felt a shame having to put my guy clothes on, but I made my way downstairs to say goodbye to Daddy. He kissed me goodbye and couldn't resist one last play with my booty before slapping my ass as I made my way out.

'You'll have to tell me your name before we meet again,' I called to him as I made my way to the car before driving off. I couldn't believe what I'd just done; I just fucked a guy who came inside me, and I didn't even know his name. But hey, the massive smile on my face showed I didn't really care.

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Really hope you enjoyed it, please leave me some comments and feedback about whether you'd like more. Thanks!