Panty Boy Diaries: Entry 01

This is the first entry in what I'm choosing to call my Panty Boy Diary. It is a true story of the first time I gathered the courage to meet with a dominant black man. I will do my best to make this as accurate a retelling as possible. This is also my first attempt at publishing my writing so please go easy on me. I welcome any and all feedback/thoughts/opinions about both my writing style and the contents of the story itself.

Now that that's out of the way, let's get started shall we. I'd like to begin by providing a tiny bit of background. I am currently an early 20's Asian male living in the great city of Toronto, Ontario, Canada. I'm 5'10 and was 180 lbs when this story takes place. I wasn't overweight and wasn't chubby at all because I work out a lot. Most of my body was well toned.

In my day-to-day life I am as masculine as can be, both in terms of looks and behaviour, but behind closed doors I have a huge fetish for lingerie. I love the way that it enhances the femininity of the wearer without taking away from the appeal of the naked female body. I would always find myself looking at what the latest trends were with supermodels, and when I watched porn I prefer the porn star to be wearing some kind of sexy outfit rather than just being naked. This obsession would lead to me ordering my own pair of panties online as I eventually grew curious of what it would feel like to be the one in the sexy g-strings and thongs. The very first pair that I would try on was a bright pink g-string with a lacy front. I loved how girly and slutty it was. It was such a huge turn on to try on something that I could only imagine a slutty girl wearing while being plowed in a porno, and this lead to some of the best masturbation sessions of my life as my cock would be as hard as a rock while I wore them.

However, as time went on, my collection of panties would grow to the point where I had enough panties to rotate through a work week, but the allure of the panties was beginning to wane. I was at a point where I would no longer get a boner from just wearing the panties. This was unacceptable, by this point I was completely hooked on the sexual high that jerking off in panties gave me. I needed to do whatever it took to get back on that level of arousal.

I quickly got on my computer and scoured the internet (as you do nowadays) for men like myself, who needed to have skimpy panties hug their waists as they jerked their meat. I'm not going to name the specific sites and resources that I found because then the story would be way too long, but what I found was that these men (if you can even call them that), who got off on wearing women's clothing liked to refer to themselves as crossdressers and sissies. As I continued on my quest to recreate the sexual high, I quickly found myself immersed in this new found world of lace and lingerie.

Now, I'm not delusional, I know that it takes a lot of time and commitment to become a passable sissy and those are two things I don't have. Like I said earlier, I'm a masculine guy in my day-to-day life and I know that I'd never be able to become a passable sissy without outing my fetish to the world. With that being said, I was also able to learn that I share some similar kinks, that I never even knew about, with these sissies.

I can't believe I'm about to document and publish this to the world wide web. These kinks mainly revolve around emasculation, sexual humiliation and degradation and taking on the submissive role in a relationship. I now know that the reason I enjoy wearing panties is because it is the complete opposite of what a MAN should be doing. The humiliation of resigning myself to wearing slutty panties to get off is what turns me on. I fantasized about modelling different outfits (school girl, french maid, kitty cat) that are commonly associated with slutty girls. It turned me on to read the comments that some sissies would get, from the men in the online community, when they would post photos of themselves all dolled up. The comments about how they wanted the sissies to be on their knees worshipping there dicks and how they wanted to destroy there boipussies got me so aroused.

For awhile, reading those comments and discussions between daddies and sissies would be more than enough to satisfy my horny appetite, but just like it did with wearing panties, my arousal began to dissipate over time. I began to crave the attention that some of the sissies would get in the forums. I wanted to be in their position, I wanted to be humiliated and degraded.

Oh the things we do for an orgasm. After some deliberating, I worked up the courage to post an ad on Craigslist. According to the forums I lurked, the best way to get local daddies was either Craigslist or Grindr, since the contributors to the forums were from all over the world. I didn't want to risk having someone I know find the Grindr app on my phone so the logical option was Craigslist. I can't remember exactly what my first ad said, but it had to have been something along the lines of "Curious Asian boy looking for Daddies to use me." I had posted this knowing that I had no intention of actually meeting anyone, I just wanted to see what it was like to talk to men while in my submissive mindset. I continued to post ads and jerk off to the convos I'd have with horny men for about 2 weeks. During this time, I'd get contacted by a black man, let's call him J, who knew that all the ads were from me. I didn't actually know that he knew all along until after I became his bitch.

He said it was the pictures of my ass that I'd attach to the ads that gave it away. I have a mole on my left butt cheek that he used to identify that all the ads were from me. J would always email me asking me for an opportunity to be my daddy without fail. He never missed an ad I posted.

"Why don't you just come over and submit to my black cock?' would be his usual reply. This would always be accompanied with a picture of his massive dick. I could only guess that it was 8 or 9 inches as he never actually told me how long it was.

One Sunday night, I was feeling particularly horny and was not getting the usual amount of responses that I normally got. I was desperate to get myself off and go to bed as I had work the next morning so I finally gave in and responded to J.

"Convince me that you're the daddy for me," I replied. What follows is an exact copy of the email log that we had sent each other that night with some of my commentary in between.

J: What's good you sexy bitch? I saw your ad.

Me: I know, that's why I responded. Can you tell me a bit about yourself? I need to what

you're into before we meet.

At this point, I usually try and coerce the man into telling me stuff that he plans to do to me. It turns me on so much knowing that real men with real cocks get turned on by the thought of my ass.

J: I'm looking to host that sexy ass of yours at my place in Newmarket. I'm just looking to have you come over and do as you're told. Gonna bend you over and feed your pussy this black cock.

Me: Omg, that sounds hot. Newmarket is a bit far for me though, I'm in Toronto. What's so special about you that will make me want to choose you tonight?

I know, I'm such a tease. I sound exactly like a flake, and I don't even know why he continued the conversation with me. I guess when you have a dick the size of my forearm between your legs, you can afford to be confident.

J: Don't worry about distance, I'll get you an Uber. I know your ad said you're discrete, I have the place to myself. My girl is at work tonight so you can try on anything you want.

Me: What makes you so sure that I'll even agree to meet you?

J: Because I want a piece of that ass. Daddy gets what daddy wants.

No reply from me, as I'm beginning to lose interest. I just wasn't getting aroused by what he was saying.

J: Look girl, I just want you to come over and try on this outfit my girl has. You said you want a real man to humiliate you and make you submit to his cock, so be a good girl and tell me where to have the Uber pick you up.

Now we're talking. This got my 4 inch penis as hard as can be.

Me: Um are you sure? How am I going to get home after? I can't stay the night.

I said this hoping to get him to continue to be assertive with me, but at the same time I was trying to find an excuse to not meet him.

J: I'll get you a ride on the way home. You weren't going to stay the night anyway, I just want to use you. Give you my load and send you home. You're going to look so good in these.

He sends me some pics of the outfit he intends for me wear. Included is a shot of a matching bra and g-string set in firetruck red, a white blouse and a red and black plaid skirt. I'm erect just writing about it now. He had a school girl outfit ready for me and it was slowly starting to creep into my mind that I might just meet him.

Me: As much as I want to submit to your big black cock in that outfit, I have to tell you that I'm not passable by any means and I'm only willing to do anal, no oral.

This was the last attempt by my male pride and ego to talk myself out of doing this. I had given myself an ultimatum. If, after reading this, he was still ok with meeting me, than tonight was going to be the night I lost my ass cherry. Also as a side note, I can't bring myself to give another man a blowjob, it ruins my fantasy of giving up control. To give a blowjob, means that I have to choose to perform the act. With anal, the man who's got his cock in my ass is in complete control of the fucking that I'm receiving and there's nothing I can do but take it.

J: Girl, that don't matter. I ain't gonna be looking at anything but that girly ass of yours while I hit you from behind anyway.

Me: You can set the Uber pick up at ....

J: Just ordered it. Here's my number 123-456-7890

I'm not sharing his actual number for obvious reasons. After receiving this last message, I quickly got dressed in some sweats and a t-shirt, grabbed a light hoodie and was out the door. I made my way to the Uber pickup spot as quick as possible because I knew that all I needed to do was get in the car. The rest would be out of my hands, and I couldn't chicken out once I was in the car.

This is exactly what I wanted. I was about to completely submit to another man. A 6'5" black man. It was the most embarrassing and humiliating thing to be doing. I had agreed to let another man fuck me. What could be more emasculating and humiliating than feeling pleasure from having another man's dick in my ass. This was all I could think about on the ride to his place and I loved it. My little excuse for a penis was so hard in my pants. The potential embarrassment of having the driver see it was just adding to my arousal.

After the 30 minute drive, the driver pulls up in front of his house. I take one last deep breath and open the door. I take out my phone and send him a text simply saying, "I'm here."

J: Good girl, come around back.

I'm panicking now, thinking to myself that I did not agree to getting fucked in his backyard for all his neighbours to see. Thank god that this was not the case, although he did fuck me in his backyard later on but that's another story. When I finally saw him, he was on his back porch smoking a joint. I slowly walk up the steps towards him. As I approach, he holds his hand out to me while he holds the joint between his lips. Not quite sure what is about to happen, I reach out with my hand as well and we end up shaking hands.

"My names J, you don't gotta tell me you're name. I think I'm going to call you Julie," he says while he takes another puff of his joint, blowing the smoke out in my face. While all this is happening, I realize I agreed to come here without even getting his name. What kind of an idiot am I. Sensing the alarm on my face, he quickly ashes his joint and puts his hand on my shoulder saying, "Don't worry, this is going to be a night to remember. I'm gonna dick you so good, you won't be able to get enough."

I'm sure I went bright red at this statement, but it was already getting dark out so I don't think he could see. However, I wasn't as alarmed anymore because now I was just plain horny. All I could think about was what his dick looked like in person and how it would feel sliding in and out of my ass.

He proceeded to make his way into his house, and I followed. No prompt needed, at this point I had lost all control. I was in the presence of a man who exuded confidence. He was the definition of an alpha male. He towered over me at 6'5" and as much as I worked out, there was no way that I could overpower this man. I knew that my only option now was to do as he says. Submit. And that's exactly what happened.

"Alright Julie, the bathroom is up the stairs and is the second room on the left. I've left everything you need to get ready in there. You better be wearing everything I left you. You've already earned one strike for not coming over right away. Now hurry up, I want you ready in 20 minutes." Now that we were in his kitchen and the lights were on, I'm sure he could see how much I was blushing with embarrassment. "You look cute, when you're shy, but if you don't get moving, it's going to be strike 2 bitch,' was his response.

I hung my head and quickly made my way up the stairs not even knowing what kind of punishment he was threatening me with. Strike 2? I didn't even know what strike 1 meant, but judging by his tone of voice, it sounded like I did not want to find out.

When I got to the bathroom, I closed the door behind me and took a breather. Telling myself that this is what I want and that I need to stop resisting mentally because my own penis has been dripping pre-cum ever since he named me Julie. I was going to be used like a sissy slut tonight whether my male ego liked it or not. With this new found resolve, I started to look around and examine the school girl outfit J had chosen for me. The g-string was clearly not meant for a man to wear because as I slid it up my legs, even my 4 incher would not stay put, it hugged me nice and tight around my waist and the string was right up against my soon to be well fucked hole. Next came the bra which was tricky because it was the first time I ever wore one, I had to get the clasp done up front before rotating it into position with the cups over my chest. The blouse was next and easy enough, and then I stepped into the skirt before pulling it up. The skirt had a nice stretchy waistband so I had no problem getting it on properly, but it became very clear that this was not a skirt you bought at your local shopping mall. It only covered half of my ass, if I had been a regular size woman it might have just barely covered my ass, but me being 5'10" with longer than average legs, this thing was not hiding anything. Thinking that I was ready, I did one quick look in the bathroom mirror to see what I looked like, and noticed that there was also a shoulder length blonde wig resting on a mannequin head to the side of the sink. I wasn't sure if this was meant for me but didn't wanna disappoint J just in case it was, so I put it on as best as I could. As I was fixing it onto my head, I also noticed a pair of red heels on the bathroom floor, and figured that these were also meant for me. I had to really squeeze into these even with my small Asian feet (I wear a size 9 men's shoe comfortably, and can fit into 8s uncomfortably). It's a good thing these had ankle straps because there was no way they were staying on otherwise. After one final glance in the mirror, I quickly made my way out not wanting to take longer than my given 20 minutes.

I wasn't quite sure where to go from here, but I heard some noise from a room just down the hall and called out to J asking if that was him. "Yeah hurry up Julie, I wanna see how you look," was his reply and I then did my best walk over to the room in the heels. Really, it was a teeter at best, I could not walk in those damn heels. I had to hold the wall the entire time to keep my balance. Slowly, but surely I managed to make it to the room without breaking my ankles.

When I got there, I realized that this was his bedroom. He was going to make me his woman in the same bed that he shares with his actual woman, and with this thought my dicklet continued to drip. J gave me a nice long look over, and I just stood there not saying a word, not really sure what to do. I didn't know what to say or what to do because he was naked and stroking his cock. This is the first time that I've ever seen another mans boner. I've seen dicks in a locker room before, but they don't do anything to arouse me because in locker rooms I'm not in a sub mindset, I'm not Julie. This was different, I must've looked mesmerized. In reality, I was wondering if maybe this was a bad idea because I was not sure how he was going to fit that thing inside me.

"How big is that?" was what I finally worked up the courage to ask. "I ain't ever measured. You don't need to worry about it, what you need to do is put these socks on, I forgot to put them in the bathroom," was his answer as he handed me a pair of white thigh high socks with a red stripe around the top. I stumbled to have a seat on his bed to take off the damn heels so I could get the socks on. Once they were on he said that I needed to get the heels back on even though I told him they hurt my feet.

"You're not going to be walking in them, you're getting fucked in them. Now shut up, and get on your stomach on the bed," commanded J.

I was hesitant at first, but I saw the look of irritation on his face and then I found myself laying face down on his bed, with the heels on floor. With my ass hanging over the side of his bed he told me keep my eyes forward and to not look at him, not that I could with the hair from the wig in my face. While I was getting some of the hair out of my line of vision, I heard a very loud clapping noise, almost as if someone had popped a balloon. Then I felt a rush of heat on my left ass cheek and it occurred to me that I was being spanked. He continued with 4 more spanks alternating between my cheeks. I began to scream out in pain after the 2nd blow and had tried to get up and protect myself before the 3rd came down. I tried, but was unsuccessful. Almost as if he was reading my mind, J closed in and used his left arm and some of his body weight to hold me down. It didn't help that I had limited mobility in the heels (they were 4 inches from what J told me at another time). I cried out in pain for all 5 swats, and my little penis could not have been any harder. The humiliation of being spanked was too overwhelming, I couldn't help but be turned on.

"That was for not coming over right away," he said with authority. He then began to slowly massage my sore behind and this foreign feeling of having a man's hands caress me was a welcome surprise. As good as the gentle caressing was, what happened next was even better.

I felt J get up off of me, no longer restraining me to the bed with his weight, I leaned up on my elbows and looked over my shoulder at him. What I saw was not something I was prepared for or even expecting. He got down behind me and pulled my g-string to the side. "I got this outfit for my girl last year, these heels are my favourite out of all her shoes," he said before he parted my cheeks with his strong hands. There it was, my butthole, my cherry, my boipussy, staring him right in the face. "Mmm, nice and smooth. You came prepared Julie," he said as he spit on my virgin hole. He then leaned in close and slowly began to show me the pleasures that the butt can bring. He worked his tongue all around my precious rosebud. It was magnificent, I was squirming in pleasure from him rimming me. This went on for about 5 minutes, before he stood back up and walked over to his night stand.