Charlie 41

Just a heads up before anybody starts reading, this does contain light elements of crossdressing and a lot of panties being worn. Thanks for reading, hope you love it.

How do you end up in a room with three other men as they take turns fucking you? Well, if that got your attention that's the story I'm about to tell. The story of a how a young man from the north of England went from being straight, to curious, to a complete cock slut. And once it started, it all happened very quickly despite it taking me a long time to pluck up the courage to do it.

My name is Alex. Up until I was a young teen, I always thought I was completely straight. Then I made a discovery in my later school years. Being around women, and in the era of low-rise jeans, I got to see a lot of panties peeking out, lace, thong, cheeky; you name it, I saw it. Even some of the teachers, my personal favourite was my English teacher, she bent down to retrieve a pen and above her trousers was a white lace thong. I remember it vividly; the waistband was twisted, and I couldn't get that image out my head for a long time. There was also a girl who wore a thong to class one day and when it peeked out the back of her pants, it had a giant pink bow around the back. I couldn't believe someone would wear that to school. And finally, the girl with the biggest ass in the school wore tight trousers and one day in science class, she leant forward on her stool and out popped her white cotton thong. Thankfully, I had time for my boner to disappear before leaving that class. At home, I then found my Mom's lingerie, and at this point in my life, I couldn't resist trying it on. Pulling on a burgundy lace thong for the first time, my cock came to life. And from there I tried more, bras, tights and babydolls. I started sneaking them out of my Mom's room and into my drawer so I could wear them on a night.

By the time I turned 18, it had become an obsession. Girls took a backseat in my life, and I obsessed over lingerie. I was, I would say average build. No hairier than any other man, but I always thought I was pretty good looking. I had a 7-inch cock when it was hard, but when it was soft, it fit perfectly inside a pair of panties. Which I was wearing daily now. I still hadn't had sex with a man or a woman, and although I didn't want to be a virgin forever, it would be a little while longer before I finally lost my virginity. The day I passed my driving test, was the day my freedom finally begun. I could go into shops and buy more panties without the fear of being caught by my parents. I had myself on multiple dating sites, but the one I was getting the most interest from was a gay dating site. I was taking photos of my panty covered ass, and plenty of older men were willing to take my cherry, but I couldn't build the courage to do so.

At the age of 20, I had my first sexual experience. And surprise, it wasn't with a woman. I'd been talking to a gentleman on a dating site who hosted a weekly orgy at his place. I messaged and asked if I could join them one day, and he immediately told me that the guys would eat me up but if I was into older men to come along and give it a go. I wasn't sure how they'd feel about me wearing panties, so I purchased a jockstrap instead. On the day, I jumped in my car and headed off to the apartment, naively thinking that I was going to come back home having been fucked by several different guys. The moment I got there; I was instantly nervous. My anxiety got the better of me and I didn't know what to do. Luckily an older gentleman approached me, he wasn't the host, but he was naked and smaller than my 6ft 1 inch frame. He made small talk, made me stroke his cock which was a strange feeling before he dropped to his knees, pulled my cock out of my jockstrap, and put it straight into his mouth. It was great English hospitality. Now I wish, I had some epic first-time story starting here, but I hadn't been touched by anyone else before and I barely got hard before I started to spew cum into this guy's mouth. That's when the post-nut clarity set in, I panicked, picked up my stuff and headed home before regretting what I'd done.

After that, I took an extended break from the dating scene. I stayed on dating sites, trying to get myself hooked up with a woman but none ever seem interested, but that didn't bother me. I purged all my panties, throwing them away and being ashamed of what I'd become. But that feeling didn't stick around for long. I was soon back on lingerie websites, and in shops collecting orders as I started to build my collection once again. I expanded my collection and started to buy stockings, miniskirts and even some bodysuits. I was back on the gay dating site and guys were eating those photos up, I was getting complimented from every direction and I loved it. Although I wasn't physically attracted to any of them, I still fantasised about them fucking me and usually when that happened it didn't take me long to cum. Then just before the lockdowns began in 2020, I finally lost my virginity with a woman. We met on a night out, went back to her place and had sex. Yet I still didn't feel fulfilled. Then the pandemic struck, and we didn't see each other again. Being 23, and stuck at home with your parents during lockdown was a lonely place. I became very sexually frustrated and eventually bought my first dildo. I spent night after night riding and playing with myself, desperate to try the real thing one day. By 2022, I was now 25 and in a relationship. After the lockdown restrictions had lifted, I reconnected with the girl I lost my virginity to, and we started being together more and more. Don't get me wrong, I loved her, but it didn't deter me from being on the gay dating site. And I know that makes me a bad person, but somethings are impossible to resist.

Then just as we were about to go on our first holiday together, a very handsome older man dropped into my messages. I'd had him on my 'hotlist' for a long time but never bothered to message him because why would he want a first timer like me? I say he was handsome, I hadn't seen his face, his profile contained pictures of just his body. But mine was the same, he'd messaged me and wanted to meet purely from looking at my ass. He had a few pictures of his bulge, and it looked a decent size. We chatted, and even while I was away on holiday, I'd message him every night after my girlfriend had gone to sleep. He liked my panties, and didn't mind me wearing them if we ever met. That was a big thing for me, panties were a big part of who I was, and I wanted my first experience with a man to include them. It helped me feel submissive and that's because I only saw myself as a bottom. I had no interest in topping men, when I fantasised about it, I was on my back being fucked.

Compared to all the other people I'd chatted to on the site, Charlie was different. He was patient and wasn't pushing me into something I wasn't ready to do. All in all, by the time we'd arranged our first meet, we'd been talking for 10 months, maybe longer. He knew he could be patient because he had a whole list of bottoms who were eager to meet him for the first time, and after that first time, they always came back for more. The verifications on his profile told me that much. Sometimes I could jerk myself off and cum just reading how other people said there meet went with him. We lived close enough to each other than meeting wouldn't be a problem, and I teased him a few times by telling him I was working in his area, and he should look out for a guy with something lacey underneath his work trousers.

After a few months of chatting, I struggled mentally and hid my profile while I worked through some things. But again, I couldn't keep away and was soon messaging Charlie again. I talked through my anxieties, and he was so sweet throughout the whole thing. As our heated messages picked up again, he showed me more of him. Cock pictures and videos came through, and it must've have been at least 8 inches and thick. And all I could think about was playing with it but at the same time the thought of not being able to take it left me not wanting to disappoint him. But I got bold, and I wanted to see a face picture, the worst thing would be to arrive and find I'm not physically attracted to him at all. I was surprised to see his next message contained a photo of his face, seen as though I hadn't sent him one. And my jaw dropped when I saw the photo, he looked nowhere near being a man in his 40s. I would've said early 30s easily. He was so handsome, dark hair, beard, hairy chest, and a massive cock. Suddenly, I had a face to put next to my fantasy.

'When shall we meet?' I messaged him one crazy Saturday night. I still lived at home with my parents, so I'd only need an excuse of where I was going for my girlfriend.

'Are you sure you're ready?' Charlie replied.

'I want to try,' I told him. 'I want to meet you, I'm not saying I'll make it to your apartment, but I want to see how far I get.'

'How about Monday? After work?' Charlie suggested.

'Sounds perfect,' I replied. 'Hopefully I'll see you then.'

On Monday after work, I quickly headed home and changed into some casual clothes, put on some red lace panties, and headed out. I told my parents and my girlfriend that my car was booked into the garage, and I would be home in a couple of hours. I set off, it was a 20-minute drive, and I got most of the way there. The last roundabout proved to be my stopping point, the anxiety hit me, I felt sick and couldn't go any further. I had to pull over and catch my breath. I quickly pulled out my phone, messaged Charlie to say I couldn't do it and drove back home. When my parents questioned what I was doing home so soon, I just told them I got the wrong date for the appointment.

When I woke up the next morning and checked the app, I had a message from Charlie, 'don't worry about it baby girl, we'll give it a go another day. Maybe try a different approach.' That put me at ease, I still felt like I'd let him down, but it meant a lot that he wasn't being a cock about it. We continued to message for a while, my 25th birthday came and went, and soon summer was upon us. Charlie's messages seemed to slow down, he wasn't messaging me as often and I felt like I was losing out on the chance of a lifetime. I sent him some new photos, hoping to get his attention and it worked. We were back on the right track and Charlie seemed keen once more.

'Your time will come,' he said to me when I asked when we could meet.

The weather was scorching hot now and thankfully that worked in my favour, 'I'm free this weekend if you want to give it another go,' I messaged him back.

'Listen,' Charlie started his message. 'I'm always going to prioritise guaranteed meets, but I never get a meet when it's this hot. People would rather be in the beer garden.'

I quickly replied, 'I completely get that, I don't ever want to waste your time when you could be meeting someone else.'

'Why don't you come round on Saturday?' He suggested. 'No pressure, nothing sexual has to happen, it's just two friends meeting up to have a drink on my balcony.'

'That sounds perfect,' I replied. So that was that, attempt number two was locked in. And this time I wouldn't be turning back. At least I hoped I wouldn't be. I managed to get through the next few days at work without letting the nerves get to me. And Charlie messaged me during the week with his address and asked me to get to his apartment for about 12, and he should be back from brunch by then. When Saturday arrived, I woke up and I was more nervous than I had been for anything in my life. My girlfriend thought I was going out to spend the day with a friend, which I guess was kind of true. She just didn't know that the friend could well end up fucking me before I left.

I got ready on Saturday morning, and shaved my cock and balls in the shower. I thought about shaving other areas, but my legs and ass weren't naturally hairy. I did have a hairy chest though, but as much I would want that to be smooth, there was no way I could. There would be far too much explaining to do. It was set to be another warm day, and the temperature was already rising quite high before noon. A simple pair of shorts and a t-shirt would suffice for the day, and I picked out a pair of white cotton panties with a bow on the front to wear underneath. I packed a little bag containing a few more sexy items I might wear, including some lacy panties, stockings, bodysuits, and a mini skirt. The bag went into the boot of my car, and I set off. I reached the roundabout where I turned back last time, but pushed through and made my way to Charlie's apartment.

The apartment block was easy to find, and I parked up on a side street. I composed myself, took a deep breath and exited the car. I collected my bag from the car, threw it over my shoulder and began the short walk up a tiny hill to the back entrance of his apartment. I looked up to the apartment to see a handsome adonis sat on the balcony. He was dressed casually in what looked like gym wear, and had a pair of sunglasses as he sipped on his drink. I forgot that he'd never even seen my face, yet when he looked over his balcony and saw me walking towards him, he waved at me, and I waved back. He then headed inside, and I reached the door, and before I could even press the buzzer, the door unlocked, and I pushed it open and walked upstairs.

I reached the apartment door, the gold numbering signifying I'd arrive at the right one. I tapped lightly on the door with my fist and within seconds the door was opened and there Charlie was. He was a little smaller than my 6ft 2-inch frame, but his photos really didn't do him justice. He was more handsome than I could ever had imagined. Everything about him was immaculate, hair, beard, clothes, and his aftershave to name a few. He was wearing a black gym t-shirt, black gym shorts and a pair of white sports socks. He smiled to greet me, 'Alex, lovely to meet you,' he leaned in and hugged me.

'Yeah, you too,' I stuttered out. My heart was beating a million times a minute and I'd be shocked if Charlie couldn't feel that when we hugged. He stepped aside and ushered me into his apartment before closing and locking the door behind me. His apartment was exactly how other people had described it. Very well kept, clean and tidy with a hint of luxury. Out on the balcony he had small palm tree in a plant pot with a table and two chairs. Inside the apartment, it was spacious. It had a decent sized living and dining area with three doors which took you to the bathroom, bedroom, and kitchen.

'Would you like a drink?' He asked as he approached me from behind and put his hand on my lower back.

'A glass of water would be lovely,' I said.

'Ice?' His response was quick.

'Yes please,' I said, and Charlie headed off towards the kitchen, I placed my bag down by the sofa and wandered out onto the balcony and was stood looking out when Charlie came back out and placed two glasses of water onto the table.

'Grab a seat,' he said, pulling one of them away from the table and gesturing for me to sit down.

I sat down and took a big gulp of water, hoping that would help calm my nerves. It didn't. Charlie looked across and smiled at me. I could tell that he was sensing how nervous I was. And he immediately struck up a conversation about something he'd seen on social media earlier in the day. And just like that, I started to relax. Just having a general conversation about what was going on in the outside world started to make me feel at ease. Soon we were laughing, and Charlie brought out some snacks to the table, as well as refills on our drinks. I was a lot more comfortable now than I'd ever been in someone else's company.

'You're very handsome,' he said after a while of talking about other things. 'You know that, right?'

I could feel my cheeks blush, 'thank you, you're incredibly attractive yourself. And thank you for agreeing to meet me.'

'Is that the first time you've told another man he's attractive?' He smiled, 'and you don't need to thank me, you must have had guys beating down your door for the chance to meet you.'

'It is,' I blushed again. 'And no, none. I always think people don't like meeting other guys who have zero experience.'

He got up, and moved his chair closer to me. My heart started to beat again, 'well in that case, hopefully I get to be the lucky one who gets to introduce you to this world.'

'I've been dreaming of that moment, quite literally,' I stuttered.

'Oh really?' Charlie looked surprised. 'Tell me more.'

'There's not much to tell, one night I had an erotic dream, and it was before I'd seen a photo of your face. I was being fucked, and I kept moaning your name repeatedly before you came inside me, and I came hands free,' I stopped to catch my breath. 'And when I woke up, my panties were soaked in cum. It was the first time I'd ever had a wet dream.'

'That's so adorable,' he said and moved his hand over, so it was on my thigh. 'Is this, okay?'

I nodded in response, and my cock twitched as he squeezed my thigh as though it was some sort of acknowledgement. We continued to chat whilst Charlie asked me about growing up, so I explained about how I got into wearing panties and how that took me from being straight to curious about sex with men. He also knew about my relationship and didn't mind that I'd be cheating on my girlfriend if he got his way.

'I think,' he started, 'once you've had your first, you'll be coming back for more and more. And that's when I can introduce you to some of my friends.'

I swallowed, and looked at him, smiled and turned away again. Nerves were starting to rise inside me again. I was fully aware I'd been here for an hour, and nothing had happened yet. I wanted it to, but didn't know what to do. 'I'm really nervous,' I looked at Charlie and decided to be honest. 'I know what I want to happen, but don't know how to make it happen.'

'And what is it that you'd like to happen?' Charlie asked.

'Hopefully, you'd still like to fuck me,' I said nervously.

Charlie smiled, 'I'd like that very much, I'd also like to kiss you,' he said. 'If you're okay with that?'

I looked and Charlie and nodded, almost not wanting to say yes and admit what I wanted to happen. He looked around, none of his neighbours were out enjoying the sun, so he leaned across and kissed me on the lips. I felt his beard rub against my face as our lips met. I didn't want it to end, but Charlie pulled away, and quickly checked to see if I was still okay. Which I certainly was. 'Would you mind if I used the bathroom?' I asked, trying to make it subtle that I wanted to get ready.

'Of course,' Charlie rubbed his hand on my cheek. 'I'll meet you inside, you should find everything you need in the bathroom.'

I nervously stood and started to walk towards the apartment. Charlie stood at the same time and gave me a playful slap on my ass which made me giggle with nervousness. I made my way into the bathroom and stripped out of my clothes, used the toilet, and did what I had to do. It was something I'd never done before but thankfully Charlie popped into the bathroom before I undressed to show me what I needed to do. I was in the bathroom for a long time, but thankfully Charlie was a patient man. When I was done, I put my clothes back on, not having my bag with me meant I couldn't put anything sexier on just yet. But when I exited the bathroom, Charlie was on the sofa waiting for me.

He smiled at me, and I thought he was going to pat the seat next to him but instead he patted his lap. 'I'm heavy,' I warned him. But he quickly dismissed that and suggested I sat on top of him with my knees either side of him. I was more used to my girlfriend doing that for me, but I knew what he meant so I climbed on top of him. I couldn't believe I was doing it; I was just doing my best to dive headfirst into whatever was planned to stop me backing out. As I climbed on top of Charlie, we started to kiss again. This time though, the kiss didn't end. Charlie's hands ended up squeezing my ass and then he pushed his tongue into my mouth which I reciprocated. I quickly found myself grinding myself against his crotch while he squeezed and jiggled my ass. All thoughts of my girlfriend had disappeared from my mind as I put my hands on the side of his face as we kissed, feeling his stubble against my hands and face.