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 Escort Sarıyer 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 Silivri escort bayan 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 Topkapı escort 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.