tagTransgender & CrossdressersPanty Boy Diaries: Entry 02

Panty Boy Diaries: Entry 02


Hi folks, I'd just like to open this diary entry with a quick thanks to all of my readers. It's been an honour and a turn on to know that there are people who enjoyed Entry 1. Now it's time to get down to what you all came for (pun intended, I hope), Entry 2.

J had collapsed forward, forcing all of his weight onto me, smothering me into the bed. I could feel the pulsing of his cock in my ass, he was cumming while buried deep in me. I had felt defeated, conquered, and owned. Trapped underneath his body there was nothing I could do, "Mmm Julie, you know what this means right?" J asked as I felt him begin to shift his body off of me, his cock now softening.

"No, what does this mean?" I asked.

"First of all, the next time I ask you a question you better respond with daddy or master. Secondly, it means that you're officially my little slut," he replied as he pulled his cock out of me before giving my ass a hard slap.

"Now, get dressed. I'm calling you an Uber," J ordered.

"Yes, daddy," I replied as I slowly got up off the bed. I began to make my way to the bathroom instantly reminded of the fucking I just received as I had to adjust my walk to limit the soreness I was feeling in my ass. Finally making it to the bathroom, I began to pick up my male clothes to get dressed. As I was in the middle of getting dressed, J had walked into the bathroom and started to take a piss, not even flinching at the fact that I was still in there with him. I couldn't help but stare at his massive cock.

"That was inside me," I thought to myself, and a wave of humiliation came over me. Here I was, standing in the bathroom, freshly fucked, taking off my heels unable to take my eyes off of the cock that did this to me.

"When are you free again, bitch?" asked J snapping me out of my gaze.

"I.. I don't know..daddy," I stammered remembering to address him correctly, quickly looking away hoping that he didn't notice me staring.

"Well, my girl normally works Thursday nights, so I want you to come over later this week and be my girl that night," J said as he walked out of the bathroom, not giving me a chance to reply.

"I'll try, but I have to check my schedule, daddy," I shouted down the hall so that he could hear me.

I didn't know what to do. I didn't agree to make this an ongoing thing, I didn't know if I could bring myself to do this again. It was already humiliating and shameful enough this one time. Who knows how long it was going to take for me to recover from this. I clearly couldn't walk normally, and I was more concerned about what people would think of me when they saw me gingerly limping my way around. How was I going to sit down without being reminded of J and my reflection in his mirror as he pounded my poor behind.

I got dressed as quickly as possible trying to get out of there sooner rather than later. Now that I was no longer horny, I was beginning to regret the events of the night and becoming increasingly paranoid. "What if all my co-workers know I'm a panty wearing bitch boy for my dominant black daddy when they see the way I walk Monday morning," was the thought racing through my mind when I had left J's place.

The first thing I did when I got home was take a shower. I felt as if I had to cleanse myself of what I had just experienced, but as the water started pouring in over me and I had some time to evaluate the events of that night, I began to get hard. I couldn't believe it, despite how ashamed I was that I enjoyed being a sex toy for another man, my penis was as erect as a flag pole and showed no signs of going away. So, naturally, I began to masturbate and found that masturbating to the memory of my reflection in the mirror as J was completely dominating me was highly erotic. It might've been one of the best masturbation sessions I've ever had.

Nobody at work ended up questioning me, but the work week was a long one. Work itself went by business as usual, no hiccups, no suspicions, just work. What had made it a long week was that I found myself having thoughts of Sunday night over and over again. Thoughts about how I had fully surrendered something as symbolic as my butthole. Along with my virginity, I had surrendered my manhood, my masculinity. I couldn't stop myself from thinking about how taken I had felt, and ultimately, how good his cock made me feel.

That's when I knew I was going to see J again on Thursday night. I set aside my male ego and told myself I would trade my masculinity and dignity for the sexual high I experienced as a sissy for at least one more night. Hoping that maybe, just maybe, J would make me cum handsfree with his cock in me, like a girl. Which, to me at least, might actually be more humiliating than being fucked by a man.

I actually didn't end up hearing from J again until Wednesday, when he texted me telling me to be at his place by 7 PM. His reasoning was that he wanted to have me for longer than he did on Sunday night.

"Yes, daddy," was all I sent in return.

What J had sent me back in return was something out of a sissy fantasy.

"Come in through the front door. Your outfit will be on the coat rack, make sure you change before you see me. I don't want to see you in male clothes anymore, you're not a man when in my house," was what his text read. At this point, I began to think maybe this could be an ongoing thing. I absolutely loved just how turned on I was getting by simply reading his text message. It seemed as though he knew just what to say to get me back in a submissive sissy state of mind.

6:55 PM, Thursday evening, I found myself opening the front door to J's place. True to his word, there was a large duffle bag hanging from the coat rack. As I grabbed it, a note had fallen out of it and landed in front of me on the ground. It had instructions that read, "Take this to the bathroom upstairs and get ready. I want you to put on everything in the bag and make sure you're pussy is nicely lubed."

Putting the note back in the bag, I made my way upstairs to the bathroom. I had to stop and take a breath as I closed the bathroom door behind me. "I'm really doing this again. What was I thinking? What did I get myself into?" were the thoughts that were racing through my mind as I started to panic. The conflict within me was rising. On one hand, I live my life as a man. My interests are mainly sports and video games and other typically popular things amongst men, but on the other hand, I really enjoyed being dominated by J's magical black cock. It's like it cast a spell on me.

"Alright, you're already here. You enjoyed it last time, you'll enjoy it again tonight. If not, you never have to see him again, and nobody will ever know that you've taken cock in the ass twice," is what the conclusion that I eventually came to in his bathroom.

With my mind made up, I opened the duffle bag and began to empty it's contents. What I had found inside for tonight was a pink leather mini skirt, a pair of pink boy short panties, a white top that had "Daddy's Little Girl" written across the front in pink lettering, a pair of white stockings with lace tops and a pair of open toed hot pink high heels. I began by pulling on the tight panties, they seemed to hug my butt really tight and I have to admit, they made my ass look real good. In any other reality, I would love to fuck a girl who's ass looked like this, but alas it was me who was getting ready for the fucking. This thought reminded me that I needed to lube up for J, and so I took off the panties and grabbed the lube from the bag.

Lubing myself up, preparing to be taken is a sexual activity in itself. I began by just smearing as much as I could around my hole before realizing that I would need plenty inside my hole as well. This lead to me to begin fingering myself. First with just one finger, but I quickly got carried away with the feeling of being penetrated and inserted 2 fingers. It wasn't until I managed to work 3 fingers did I realize that I wasn't completely recovered from Sunday. I felt the familiar soreness of being stretched when I had began working the third finger into myself. I quickly pulled my fingers out, frightened by the feelings I was having. I was enjoying the soreness and the pain of stretching myself out. This is not something that a regular straight man feels, and that scared me.

Hoping to get my mind off of my masculinity, I quickly pulled the panties back on. I did not want my male ego or my dignity getting in the way of recreating the sexual pleasure I felt in my backside last Sunday. I followed up the panties with the top before I sat myself down on the toilet and made my first attempt at putting on stockings. To tell you that I got them on without a hitch would be a lie. I had accidentally ruined the left stocking. I still don't know how it happened, as I was being as careful as possible, but I did have a slight tear on the outer half of the left stocking. It wasn't huge, but it was definitely noticeable. I smiled as I managed to get the right one on without ruining it, but again I thought about how a real man would never have this thought. A real man would be the one ruining a girl's stockings in the bedroom.

In order to dispel these thoughts, I reached for the pink leather mini skirt and began to step into it. Getting the skirt up and around my waist was a welcome challenge. I had to twist and turn and shimmy and jiggle just to get it around my waist before zipping it up at the side. The makers of this skirt did not have convenience in mind when they made this. It was so tight that it restricted my stride. I had to take smaller steps to be able to get around in this thing. Although, what it lacked in convenience for the wearer, it made up for in convenience for admirers. Similarly to the plaid school girl skirt from Sunday, this skirt did not cover my ass whatsoever.

The heels must've been at least 5 inches. They definitely looked higher than the red heels I had worn last time. These were also my size, shockingly. I did not have to squeeze into them at all. They were a perfect fit. I simply slipped my feet into and did up the ankle strap, no issues at all. I couldn't help but suspect that these were bought just for me. This kind of flattered me, he remembered my complaint last time and went through the trouble of making sure my heels fit.

I didn't notice I was blushing until I looked in the mirror. Before I did look into the mirror though, I had gotten the wig from inside the bag and put it on as best as I could. This is when I checked the mirror and caught myself blushing. Once again, I thought to myself, "A real man would never be caught dead wearing this outfit, let alone get fucked in it."

"Well, it's like J said, in this house, I'm not a real man," was my final thought before I exited the bathroom and made my way to his bedroom. Unfortunately for me, my trek to his bedroom in those heels was all for naught. He was not there, and there was nobody else on the floor, so I was now forced to go down the stairs in my 5 inch heels. Thank god for railings is all I have to say about that adventure.

When I had finally made it to the main floor, I decided that it's best to just find him as quick as possible. That way I wouldn't have to struggle so much with my masculinity anymore, I could just submit and give up control to J.

It took some searching, which wasn't helped by the heels or the skirt restricting my stride, but I eventually found J in what appeared to be his living room. He was seated on his couch just casually watching the Blue Jays game. Oh, did I mention he was naked? Despite having already seen everything this man had to offer, it still shocked me just how comfortable he seemed to be. Even when I'm not wearing, basically, an all pink outfit with my ass lubed and ready for cock, I wouldn't feel comfortable being naked in front of someone I barely knew. That clearly wasn't the case with J, he felt completely comfortable sitting there in front of me, in fact he was more than comfortable. Almost as if on command, his cock began to stir and stiffen up a bit. It began to grow as he took his eyes off the television and eyed me up and down.

"Mmm, you look great. Are you ready for some of this?" he said as he licked his lips and looked down towards his growing cock.

"Yes, daddy," I said as I shook my head lightly. There I stood with my legs together as the skirt did not allow me to spread them too far apart.

"Alright," was all he said as he got up from his seat and left the room for a bit.

Not knowing what to do, I began to follow him, but hearing my heels click on his floor, he quickly turned around and told me to wait right where I was and that he was going to be right back.

When he returned he had a large yoga mat in his hands and placed it on the floor in front of the TV, which was still playing the game (2-1 Jays in the bottom of the 3rd inning, if anyone was wondering).

"Get down on all fours and pull that skirt up a bit," was what he told me to do when he had finished arranging the mat. It was a bit of a struggle to get down on my knees in that outfit, but I eventually managed to do so. The whole time I was thinking about how considerate he was to get a mat for my comfort. When I was in position, I reached back with my right hand and did my best to raise my skirt up for him to enter me.

"I've been waiting all week to get back inside you. If felt so good last time," he said to me as I felt the helmet of his cock press up against my hole. He was now leaning over me, as I could also feel his chiseled stomach on my back. He didn't seem to be in a rush to penetrate me since he wasn't applying any pressure or making an effort to enter me. He just left the tip of his cock against my hole. I didn't dare turn my head to see what the hold up was but this wait was driving me crazy. To be so close but so far away, I couldn't stand the anticipation. There was no doubt in my mind at this time, no thoughts from my more masculine side telling me to stop. I simply wanted him inside of me. I wanted him to give me the pleasure that he did last time.

I then heard him reach over to the nearby coffee table and pick up a piece of paper. He held it out in front of me. I didn't know what he was trying to show me at first, but as I began reading, I realized just exactly why he was waiting to enter me. It was a test paper that he held in front of me. The results to his latest sexual health test. It said that he was 100% clean. That's not what I was thinking about when I had finished reading the paper though. I just realized then, that I was feeling the actual tip of his penis press against me. He wasn't wearing a condom.

Now that I had realized just exactly what he planned to do, I tried to get away as I was initially scared, but once again J showed me just how much more powerful than me he was. He dropped the paper and placed both of his hands on my hips and pulled me back. He pulled me with so much force that his cock popped right into me, and it hurt. I screamed out in pain and fear as the head of cock pushed into me with ease.

"Let me go!" I shouted.

"Calm down. Look at the date on that test, I'm clean. I got it because I liked fucking you, and I want to continue to do so, but it's much more fun bare. I wanted to prove to you that I'm clean, and if you want to continue beyond today, I'm going to need you to get a test too. I can't risk giving anything to my girl," J explained.

I was silent. It's not that I was speechless, I just couldn't physically make a sound, I was way too concentrated on relaxing myself to accommodate the intruder in my backside. I was doing my best to help relieve the pain I was now feeling from being so forcefully taken. There was also the realization that there really is nothing I could do to get away from J once he had set his mind to fucking me, and despite the pain this was a huge turn on. I was hoping that he didn't notice my penis starting to grow as it would come across as a sign of me enjoying this forced submission (although thinking back on it, he never forced me to get dressed or present myself to him for breeding).

"Listen, I'm not going to force you to continue. I only want to fuck willing bitches, so if you want to continue than we're going to do it bare and you're going to get tested," he said sternly to me, breaking my train of thought.

"Now, do you agree to these terms?" he asked before letting go of my hips.

"If you don't want to continue, now is your chance, you can get up and get dressed, and we'll end it at that, but if not..." he continued.

I didn't let him finish the sentence though. To this day, I do not know what had come over me, but it was clear that I had desires to be a sissy. I found myself slowly rocking back onto his cock, taking more of him into me. Now is when I did finally turn my head to see his reaction and what I saw was a powerful, dominant black man smiling down at me. He was my dom, my daddy.

"I knew you couldn't resist, you want this black dick to breed you?" he asked as he placed his hands back on my hips, once again taking control.

Yes, daddy. Make me your girl," was the only thing I could even think of saying.

With that he gave me one powerful thrust and had his whole cock inside me. This caused me to moan out in both pleasure and pain. He seemed to remember just how I liked to be fucked. This thrust allowed the entire length of him to rub against my sweet spot, and made my eyes feel like they had rolled to the back of my head. This is what I came for, the reason I was willing to trade my dignity for another night with this wonderful cock inside me. From what had just transpired, I would probably find myself in this very position quite often moving forward. Especially since I just agreed to let him breed me. I was going to carry another man's seed, and this was all I could think about the rest of the night.

"I'm glad I didn't waste my money buying you this outfit," he said as he began to find a nice rhythm of fucking me. I didn't even bother responding, I just hung my head and concentrated on my sweet spot. The thickness of his cock and the veins would rub against me with every stroke of his cock and I was going nuts. He was taking his time, almost like he was making love to me, but I knew better than that. I was only there for his pleasure, and he just so happened to want to stretch out his pleasure for the time being. His stamina was amazing. He continued at this slow pace for the ENTIRE baseball game. I was squirming and doing my best to push back onto him harder to get him to pick up the pace because my pleasure had become stagnant. I wanted it to build, I wanted to feel more of his cock against my prostate. I was getting restless. I needed a hard fucking.

"Slow down Julie, we got all night," he eventually said realizing just how desperate I was getting.

"Please, fuck me!" I shouted at him.

"Don't raise your voice with me slut," he shouted back as he grabbed my head by the wig and pulling my head back, forcing me to arch my back.

"You're MY bitch, you do what I say. Is that clear?" he stated clearly right into my ear as he leaned forward. I could now feel his breathing on the back of my neck.

"Yes, I'm sorry daddy," I whimpered in reply, knowing that a whimper would be more appropriate for someone in my position.

"Good, now be a good girl and just enjoy this dick," was the last sentence I remember him saying before he fucked my brains out. Now that the game was over, I was getting his full attention, and I was not complaining. I was moaning, grunting, oo-ing and ahh-ing in sync with all of his thrusts in and out of me. I normally enjoy sports, but found myself not even paying attention to the highlights being shown on his television. I was too lost in my own world. Every time he bottomed out inside me I would feel that he was fucking the man out of me, and it felt wonderful. This man knew how to fuck, he was hitting all the right spots and I even began to leak some pre-cum out of my sorry excuse for a cock. There was nothing more appropriate than me getting 'wet' while he was fucking me.

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by_pdy_© 4 comments/ 19239 views/ 15 favorites

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