Panty Boy Diaries: Entry 03

Does she know? Can she tell that I just got fucked? She must be able to smell the sex on me, right? My mind is racing as I sit here in this Uber on my way back home so that I can make it to my dinner with friends on time. The driver is a nice, middle-aged woman who's doing her best to be nice and polite. She asked me to sit in the front seat as she feels more comfortable having her guests seated there, and now we're talking about her full-time job as a real estate salesperson. I'm doing my best to act as normal as possible in this particular situation, but I don't think it's going all too well.

To make matters worse, I'm wearing a pair of women's sweatpants that J threw at me when he was ushering me out of his house. I'm not sure if this is just a mental thing, but they feel really tight around my waist and thighs. The legs of these sweats also only go down to mid calf on me, which I think might be able to pass as a fad, but I feel like she can see the lines of my thong around my waist and chastity cage outlined through the fabric of the pants.

These are the thoughts that were running through my mind for the entirety of that 30 min car ride. Thinking back on it, she must have had some idea of what I had spent my afternoon doing. First of all, the Uber was called through J's phone and it can't have been hard to realize that he called me the ride. It's probably no big deal though, since I never saw her again. Is it safe to assume that you guys are wondering just how I managed to get myself into this situation? Seated in a car with a random stranger, wearing women's sweats, locked away in chastity. Well let me kindly explain.

It was a nice warm Saturday morning here in Toronto. I was minding my own business going about my usual Saturday routine. I was getting ready to go to the gym as I pride myself on being able to stay relatively fit. Two nights earlier, on Thursday, I had another session with my daddy, J. I'd been seeing him about once a week for a few weeks now, but I was very surprised to see him text me so soon after our most recent session. He would usually use me on Thursdays while his girlfriend worked and I wouldn't hear from him again until the following week when he would confirm the time that he wanted me. The text basically said that his girlfriend had Saturday plans and that he wanted me to come over as soon as I could. Knowing that I always worked up a sweat during our sessions, I gladly ditched my plans for the gym in favour of being impaled on his cock.

This was going to be the shortest gap between sessions that we ever had, and I was very excited to be getting another fix of my need for submission this week. I was getting more and more comfortable with my role and the relationship that was forming between J and I. He hasn't let up. He knows just what to say to keep me in my sub space. I still haven't been able to achieve the ever illustrious hands-free orgasm yet, and I'm not sure if I was going to as the physical sensations of being fucked were never really quite as high as they were the first couple times that I had been fucked. However, even though the physical sensations were sort of plateauing, the mental stimulation was at an all time high. I lived for the sense of emasculation and humiliation that I felt when in the presence of my daddy.

Since I was getting ready to go to the gym before I got daddy's text, I made my way over to his house wearing my gym outfit. I had on some running shorts and a plain white t-shirt to go with my trainers. I decided to take the bus to his house this time since the weather was nice so it took me a little bit longer than usual to get there. I could tell that he was getting a little impatient because I was getting texts repeatedly asking me where I was and how long it was going to take me to arrive. This made the wait that much better for me. Knowing that he would probably be riled up by the time I get there probably meant that he would have a hard time keeping his hands off of me.

"I'm walking towards your house now, daddy" I texted him.

"Good. Skip the bathroom today. Get dressed and meet me out back" was his response.

This had me a little bit worried. As I mentioned in one of my earlier entries, I did not want to get caught by anyone. As comfortable as I was getting with him, this aspect of my life is still very much closeted. Discretion is an absolute must for me, so I was not looking forward to having to step out onto the porch in his backyard while dressed.

Despite my reservations, I didn't want to risk another spanking as I definitely learned my lesson the first time that he punished me. I made my way into his home and grabbed the usual duffle bag off of the coat rack as I closed his front door. Remembering that he asked me not to waste any time by going to the bathroom to get dressed, I just started to get undressed right where I was. When I was naked, I opened up the bag, quickly found the lube and wasted no time prepping myself. I made sure to use plenty of lube as well. Contrary to my previous belief, my pussy was not getting more accustom to taking a cock as big as J's. It still hurt every time he entered me, but it hurt so good. Sorry, I'm getting a little carried away here. When I was done prepping myself for daddy, I then got dressed as quickly as possible. The black thong could not have been up my legs any faster. Black stockings, ruffled black miniskirt and long black wig followed. There was no top to the outfit today. So I finished the look by buckling myself into my special lockable black heels. Those things were 6 inches of heaven.

Following the orders that were presented to me, I now made my way to the back of the house. I already knew what J was doing, as I could smell the joint that he was smoking. When I made it to the back screen door I could see that he was seated in a chair on his porch. He had a joint in his mouth and a drink on the table in front of him. I was still too afraid to step outside while dressed and so before walking out that door, I verbally announced my entrance.

"I'm ready, daddy" I quietly said.

He turned his head, looked at me a bit, and then exhaled a cloud of smoke before putting out the joint.

"Come on out, it's nice outside today" he commanded.

I knew there was no way for me to change his mind and so I just accepted my fate and stepped out onto his porch. I could feel the sun on my skin and I felt very aware of my surroundings. My eyes were constantly darting around making sure that none of his neighbours were peeping over his wooden fences. When I finally figured that the coast was clear, I made my way over to J and stood by his side as he remained seated.

"Atta girl. Scoot over and stand in front of me right here" he directed me.

I was now standing in front of him with my back towards him. He was running his hands up and down the sides of my legs when I felt him stand up. He reached around me and grabbed his drink with one hand and took hold of my poor excuse for a cock in the other. After taking a healthy sip of his drink he told me that he didn't like seeing my cock, and that we had to do something about it.

"Stay still, Julie" he sternly ordered as I heard him fidgeting with what sounded like a package behind me.

Knowing my place, I did as I was told. I then felt his chin resting on my shoulder and both of his hands made there way down to my little tool. I looked down and saw that he was now maneuvering me into a tiny pink chastity cage. Once in place, I heard a click and watched intently as I was now locked up. I had the all so familiar feeling of being owned. It was as if I was his pet and he just put a collar on me.

"That's much better don't you think?" he asked.

"Yes, daddy" I said meekly.

In reality, I wasn't really sure how to feel. I was a bit scared to tell the truth, but I didn't have much time to think about it because I soon found myself being forced to bend at the waist as J was now pushing me forward onto his table.

"Keep those legs straight. Sissies bend at the waist." was his next order.

Once my upper body was splayed out on the table, I heard J moving his chair out of the way to clear some space I suppose. He then told me that he was going inside to throw out his drink and that I had better be holding this position when he got back. I took this time to check my surroundings again. Making sure that nobody was around to witness my servitude to this man. I was definitely grateful that there was no top to this outfit as I could feel the sun beaming down on my back. Feminine tan lines would be very problematic for me to say the least.

The next thing that happened absolutely terrified me. When he got back, he quickly proceeded to secure my legs at the ankles to the legs of the table with some straps. My arms were then forced behind my back and cuffed together. I was completely restrained and somewhat panicking. I didn't dare make a noise though. This is because my fear of being caught was greater than my fear of being restrained.

"Daddy, please" I begged.

"Don't worry, you'll get what you came for" he responded right before he placed the head of his cock at my entrance.

I involuntarily let out a little moan. I couldn't help myself. I guess my body now associated any pressure on my rosebud with moans of pleasure.

He then began to rub his cock up, down and all around on my hole, but did not put it in me. He loved teasing me like this. I think it's because he knew that I needed the mental stimulation. I need to be completely humiliated while I'm being made to submit. After the rubdown with his cock, he started tapping it on my ass like he was knocking on a door.

"You know what, on second thought, I think I need to go get another drink. I'm just gonna go to the store and restock" he nonchalantly said.

"No, please don't leave me like this" I pleaded with him.

"You don't seem too interested right now. You've been really quiet since you got here and I just feel like you don't want it enough. It's turning me off" was his reply.

Since I was essentially pinned to the table, I couldn't see him, but I would bet my life that he was smirking mischievously down at me as he simply rested his man meat on my lower back. Just leaving it there for me to take in it's weight, to feel the heat that was emanating from it. He was obviously lying about being turned off, I could feel just how hard he was. It's such a turn on knowing that he had me exactly where he wanted me. I was struggling greatly trying to resist. I didn't want to give him what he wanted. I had too much pride, or at least as much pride as one can have while dressed like a slut and tied down to the table. This feeling of resistance was short lived.

"Alright then. Hang tight, I'll just be 15 minutes" he taunted.

"No! Please daddy, give it to me. Use me as you see fit" I begged. I said this louder than I wanted to as well, and now was worried that I might have drawn the curiosity of his neighbours. Even after my pleading he still didn't react. I didn't want to be left out here any longer, so I decided that my only way out was to just give in.

I started to wiggle my ass to the best of my ability.

"Please! Breed me, daddy!" I said in my most submissive voice.

"That's better. Because I'm so generous, and you asked so nicely, here" he said right before he started to enter me.

He paused for a moment with about half of his cock inside of me.

"Ahem" he was clearing his throat during this pause.

Curse this man for pushing all of my buttons.

"Thank you daddy" I responded, giving him just what he wanted to hear.

"Good girl" he replied.

He then proceeded to slide the rest of his length into me. I started to feel that familiar pain again. I was being stretched out by his manhood. I'll never forget how I felt when he was stuffing me. So full. Physically, it was pain beautifully mixed with pleasure. Mentally, the fact that this was not an act of passion, but instead an act of domination and degradation was so intoxicating. Then I felt it. He was all the way within me. The fronts of his thighs were resting on the backs of mine. Rather than simply slide out this time, he made a circular motion with his hips and started to move his cock inside of me without taking any of it out.

"Uhhhhhh" I moaned very loudly.

It was as if he was trying to rearrange my inner organs. I find myself saying this a lot, but I couldn't help myself. I was making noises that I didn't know I could make. I couldn't control the volume with which I was making these noises and it terrified me. I felt so helpless. This man was once again having his way with me. He had managed to ever so slightly manipulate me to bend to his will. I was like putty in his hands.

Right after the first thrust, is when I was reminded that I was also locked in chastity as I felt my new cage tap against the wooden table. This was just a little bit frustrating, but it quickly become another reminder that I belonged to him. Every time he would bottom out in me, the weight of his thrusts would carry me forward and cause my chastity to bang up against the table. A constant tapping that was in sync with my pounding. Another cue that never ceases to get me hard when I think about it.

My moaning, his grunts, and the tapping of my chastity were making it very hard for us to remain discrete. If any of his neighbours had walked outside, they would have certainly heard us, and it wouldn't have been difficult for them to figure out what they were hearing. The noise and my prior knowledge of J's stamina had me replacing some of my pleasurable thoughts with worried ones. I realized that there was a very real chance of someone seeing me getting fucked like this and I can't really describe it, but this sense of fear mixed with the feelings that I was getting from J's big black cock created some sort of thrill within me. I've read about a phrase online from other sissies and I think I fully understand it now. This feeling I had, must have been what it was like to be cock drunk. I couldn't think straight when I was being fucked by him.

Sadly, this feeling came to a rather abrupt, bittersweet ending. His phone began to ring. I didn't even realize that his cell phone was anywhere near us. I don't know exactly where it was but it must have been nearby because he didn't miss a beat as he answered it.

"Hello?" he answered.

In and out his cock went. I can't remember exactly, but I think he gave me another couple of thrusts before he slowed his pace and left his cock impaled in me.

"When do you need me?" I heard him say.

He started to back away and I felt his cock plop out of me. After the riding that I just experienced, I couldn't muster any strength to move around. Not that I could go anywhere. I heard a chair being dragged towards to the front of the table where my head was. When it was finally in sight, I could see that it wasn't a chair, but a stool. He set it right in front of me and raised his free hand and put a finger to his lip as if to shush me. Not wanting to be caught, I did not need to be told twice.

"I just stepped out on the porch to have a smoke. Getting nice and comfy" he said into the phone.

While saying this, he winked down at me and placed the tip of his cock right up against my lips. I hesitated at first because it had just been up my ass, but he continued to push it forward. I couldn't move so I had no choice but to comply. I opened my mouth and let him in. To my surprise, it was not a blowjob that he was after. He only pushed the head of his cock in my mouth and then just left it there.

"Yeah, I'll be there. I just need to finish up some chores that I started" he said before he ended the call.

The end of the call did not mean the end of his cock in my mouth.

"Sorry, babe. I had to make sure that you kept quiet during my call. Can't have my girlfriend hearing you beg for this black dick. I will say that you look cute with my cock in your mouth. Those are definitely DSLs" he went on to say while leaving his cock head inside my mouth.

I would later find out that DSLs stands for dick sucking lips, but that's tangental.

"I gotta go pick up my girl soon, so we need to pick up the pace. Get the tip nice and wet that I can just get right back up in your pussy" he ordered.

Not wanting him to go in dry, I started swirling my tongue around his cock trying to generate as much saliva as I could to moisten him up. Once he was satisfied, he quickly pulled out and roughly re-inserted it in my ass. I clenched my teeth because of the pain that this caused me. It was very clear that he only had one thing on his mind now. He wasn't playing games with me anymore. There was nothing psychological about this treatment. It was purely physical, he was trying to make a deposit in his cum bank as quickly as possible.

It was only about 5 or 6 minutes worth of fucking, but it was incredibly forceful. My rear end was on fire from the speed and force that he was putting into his thrusts. When he finally came, I couldn't even feel the ejaculation because I was just too sore to feel anything else but pain. This was the definition of being used like a fuck doll.

Once he was done with me, he unstrapped my legs and let me out of my handcuffs. Before I could even find my bearings, he was gone. Already back inside his home. I quickly followed him inside as I didn't feel comfortable being outside alone dressed as I was. I was about to sit down on a seat in his kitchen when J physically stopped me.

"What are you doing? You're going to get cum on my seats" he shouted as he took hold of my arm preventing me from sitting down.

"I'm sorry, daddy. You were just too much for me, I need to sit down to get out of these shoes" I apologized.

"Here, bitch" he replied as he tossed me a cloth.

This takes us back to the beginning of this diary entry. The cloth he threw me was not actually a cloth, it was the running shorts that I wore when I came to his home. Absentmindedly, I placed what I thought the was just a cloth on the seat and sat down. As I leaned forward and reached down to let myself out of my heels I realized that I didn't have the keys. I had left them in the duffle bag at the front of the house. So, I made my way to the front to grab the bag and decided that I should just get my clothes as well. Since J was in a rush to go pickup his girlfriend, I thought I'd save some time and get dressed in the kitchen after I was out of the heels.

"Daddy! Did you see my shorts?" I shouted out to him.

"No, you better hurry up and find them though, you gotta go" he shouted back.

Not wanting to disappoint him and risk getting another spanking, I just made my way to the kitchen with my shirt and the bag. I unlocked the heels and took the wig off before placing them back in the bag. Next came the skirt and stockings leaving me in just the thong.

"Why aren't you dressed? Hurry up" he said as if to usher me out of his home.

I got up and put my shirt back on. That's when I saw it. I looked down at the seat to see how much cum was leaking out of me and I saw that it was a decent amount. That's not the surprising part, the surprising part was me realizing that I had just leaked cum right onto my shorts.

"Um, daddy. Do you have some pants I can borrow? I don't think I can wear mine" I said to him as I held up my cum stained shorts for him to see.

"Ha" he laughed.

"Nah, I ain't got nothing for you. Hold on though" he said as he walked out of the room.

When he came back, he tossed what appeared to be some sweatpants at me.

"You can borrow my girls dirty laundry. Ain't no sissy borrowing my clothes" he remarked.

I was in the process of examining the pants to determine just how visibly feminine they were. I wanted to see if anybody would be able to tell that they were women's pants.