First Sissy Experience

"Well, here goes another night of intense sexual frustration..."

I've always prided myself on being able to be very sexually open minded, adventurous, and generally just not boring in the bedroom. All the while not letting sex run my life or be my motivation for anything. I've never been a cheater, and was never even a fan of one night stands, with the only ones even on my record being just experimenting with guys after girlfriends breaking up with me. While normally I like playing the dominant role in bed, going as far as my partner is comfortable or willing, I quickly realized with guys I was the total opposite. I still don't totally understand why I am that way(besides maybe just liking the dom/sub dynamic and wanting to experience both sides), but I didn't fight it at all nor was I ashamed, though it would end up taking me almost a decade before publicly coming out as bisexual. But just as I was with girls, I still wasn't an outwardly sexual person and the amount of single nights with guys was very small in number, and I was content with that. That is, until I discovered a new kink that I was very much into.

I'm not sure what prompted me to try in the first place, but it all began one day when my girlfriend at the time was at work and I decided to try on her panties. Through all the kinky stuff I'd ever done, I never once thought any of it was odd enough to make me feel like I was doing something wrong. But I felt like I had broken some huge unspoken rule when I put those panties on. They were nothing special, just a blue and white striped thong that definitely did nothing to cover or hold in my junk, but for some reason I felt good in them, sexy even. From that point on, whenever I was in the mood and my girlfriend was out, I'd start trying on different things. Looking back I wish I would have tried some actual clothing as well, but I was to enthralled by seeing my body in various panties, thongs, bras, and of course what quickly became my favorite thing to wear, thigh high socks or stockings.

Sadly however the day came though where she and I split up. It took some time, but eventually one night when jerking off, I found myself wishing I had some girl clothing to wear. After several incidents like this, one night while drinking I did a little bit of "Tipsy Online Shopping" and ordered myself some outfits/clothing and even a couple toys. The night they arrived in the mail I immediately started trying them on, checking myself out, and feeling pretty good about the whole thing. Then it clicked with me that not only did the alcohol get me brave enough to order the clothing, but also decide out of nowhere to buy the toys. I was honestly pretty nervous about them, because I'd never before this moment used any kind of anal toys alone and on my self. Like I said before, I was no stranger to hooking up with guys and taking it in the ass, but something about having my ass played with while wearing the girly clothes felt incredibly different and I become borderline obsessed with it. I was still myself and not every night was filled with me wanting something sexual from someone, but whenever I was in the mood now it came on way more intense than it ever had before. Sometimes I felt like I'd go crazy from the feeling of NEEDING to get fucked, an emotion I was not familiar with at all.

One day though, I finally made the leap. Nothing seemed special about the night, just another night where I found myself wanting nothing more than to dress up and have some guy fuck me. I had gotten familiar with online personal ads and hook up apps during that time, but before this night never had the courage to respond to anyone or post myself. I couldn't take another night that'd end with me debatably more sexually frustrated than I was at the beginning of it, so I finally made an ad. I had plenty of pics to choose from my many nights playing alone, and by this point I was familiar with the term sissy, and wrote up a paragraph that the old me wouldn't have ever even considered writing. I wanted to portray myself as a slutty femboy that wanted nothing more than to be someone's personal fuck toy. I got way more responses than I was expecting, and was honestly overwhelmed, but I eventually found someone who seemed a good candidate.

He looked like your typical white college athlete. Young, on the taller side, fit to the point he had a six pack, but most importantly his dick was amazing looking. I couldn't stop looking at the pictures he sent and fantasizing about being a slave to his cock. The shape of it was perfect with a gradual curve, a thick girth but still proportionate to the 8" length, and a head that couldn't be more perfect. After talking back and forth a bit, sent him my address, but did make it clear that it had been awhile since I'd been with a guy, so while I still planned on being a little sissy slut, he'd have to take it easy just at first until I felt more comfortable. Though feeling nervous, I was mostly excited to finally experience getting fucked in the clothes I'd come to love. Little did I know however, that this wouldn't be like any time before just with different clothing added. I was about to learn what presenting myself as a slutty, submissive sissy was going to earn me.

I didn't have much preparation to take care of in the 15 minutes it would take him to arrive. My body was already silky smooth from nights of playing alone and my ass cleaned out from playing with toys earlier that evening. All that needed to be done was put on the outfit he liked best from my pictures and position and present myself in the way he had requested. I would have worn whatever he wanted anyways, but I was ecstatic that he chose my second favorite outfit. It was lingerie that was a black, nylon full body stocking. My legs covered up to the mid thigh, with a lace border followed by two lace garter pieces on both legs connected to the upper portion. My torso was completely covered in black material to my chest and upper back, leaving only my shoulders and arms exposed. One of my favorite parts of the lingerie was the collar that extended from the lace border around my chest to wrap around my neck. My other favorite part of course being the fact that it extended down to just past my lower back, leaving both my thighs, balls, cock, and ass completely exposed. Once dressed I proceeded to finish the rest of the requests he had made. I put a small, pink glass plug in that had a heart at the end, unlocked the front door, and tied myself up how he wanted(after I suggested the position tbh). This would also be the first time someone used ropes on me instead of the other way around, so I waited in nervous excitement completely unaware of what was to come.

I was at the edge of the bed so that my nyloned feet were hanging off, wrapped up like a gift waiting to get used. My legs frogtied together and unable to budge, wrists tied to the rope around my ankle, all I could do was lay there waiting with my face buried into the bed unable to look around. Finally I heard foot steps on the hardwood flooring in the hallway, then silence as he stepped into the carpeted room.

"Oh fuck yes," I heard him say quietly upon seeing his prize. I felt his presence as he moved in close behind me, my ass completely defenseless as it hung just barely past the edge of the bed, followed by both his hands on my smooth skin. I could tell he was in no rush as he took his time to slowly run his hands over my body, feeling every crevice he could. I felt violated, unable to lift my head up to even see him as he lustfully groped my body. But I loved it. I felt helpless, not knowing exactly what he was going to, but the knowledge that my body was currently an offering to him for his personal pleasure turned me on immensely.

I let out a small moan as I felt one of his hands lightly tug at the plug I had in, only to let it go so that it went back in. For a short while he continued to pull it in and out at varying lengths, listening to my soft little moans, until he finally pulled it all the way out and set it aside. "Would you like it if Daddy tasted your pretty little pussy?" I had barely finished whimpering "yes," when my senses exploded in ecstasy as I felt his mouth against me. The feeling of his tongue exploring me cause uncontrollable moaning to escape me, while I squirmed and writhed underneath the ropes. I almost thought I wouldn't be able to bear how good it felt anymore when I started hearing his voice in between devouring my ass.

"You like how that feels huh?"

"Uh-huh, thank you Daddy."

"Your pussy really is tight like you said."

"Mmm-hmmm." I could still barely concentrate from the feeling of my ass being pleasured.

"Now be a good sissy and take Daddy's cock." Finally I could feel him stand up.

Still recovering from how amazing that felt I simply muttered "please be gentle." That hazy feeling didn't last long however after the next words he spoke.

"Don't worry I'm not going to break my new toy. But if you want to be a slutty little sissy, I'm going to use you like one. You just got a nice long reward for doing nothing that you loved, and now, you're going to earn every second of it."

Once again I felt helpless, but now with fear instead of excitement. My legs bound I couldn't stand up, arms stuck against my side no matter how much I pulled against my wrists. And still unable to lift myself up to even look around. There was nothing I could do about my ass presented and waiting. His hands firmly gripped my hips, and even though I couldn't move already, this increased the feeling of being powerless. Then I felt it. The head of the beautiful, perfect cock. Going into the night I knew it'd take a bit to get used to how long and thick he was, as I'd never taken anything that size, but now I found myself being forced to fully adjust immediately.

Despite what I knew I had in store, I couldn't help but moan when he first slid inside me. My tight as squeezed against his perfect cock as it began to stretch my insides. That moan quickly became a whimper as he slowly continued penetrating deeper without stopping until he was all the way inside me. I could hear his grunts of pleasure as he held himself deep inside me, until I let out an actual whine of pain. I think for a split second that caught him off guard and he mercifully pulled out. But that didn't last long as I felt his hand spank my smooth bare ass.

"Fix that attitude. A good sissy should want their ass to be ravaged." After which he then again proceed to push all the way inside me in one thrust. Again I cried out in pain, but this time he didn't pull out and only pressed harder against me and spanked me another time. "What was it you said when we were messaging?

You wanted to be Daddy's personal cum slave, the perfect fuck toy? And I could use you as long as I like?

So you better learn to love this quick, because your pussy belongs to me now."

With that, the slow deep thrusts were over. Time no longer had any meaning. For what felt like eternity all I knew was the feeling of Daddy's perfect cock pounding me into submission. I moaned, I whimpered, I cried out in pain(this was always followed by a spank on either ass cheek.) I constantly struggled against my ropes, but nothing helped, and it wasn't getting easier to endure either. I began thinking to myself how really this was my fault. I talked big game of being this perfect little slut, and now I was being used like one, worth nothing more than a hole for a masters cock to use. It almost felt subconscious, as I don't recall actively starting this, but I found myself begging and pleading for mercy.

"Please, please, I can't take anymore. Im to tight to take your cock like this any longer. I'll do anything if you'd just have mercy." Idk if it was coincidence, or I truly sounded that pathetic, but he actually did stop fucking me and pulled out. I could feel my hole throbbing open and closed from what it just endured. But I knew it wasn't completely over as I could still feel the shaft of his cock rubbing up and down my ass. And then for the first time since I heard him walk in, I felt his hand grab a handful of my hair and pull back, lifting the front half of my body up allowing me to see. Straight ahead of me was the mirror hanging directly above my beds headboard, and despite what I'd just have done to me, what I saw turned me on.

I saw myself, still looking sexy in my black lingerie, tied up and breathing heavily. Of course he was standing right behind me, but now I could see the lustful look on his face. He stopped rubbing his cock against me and turned enough so that it shown in the mirror. It was still rock hard, eight perfect inches of thick meat. It may have just been because I could feel it against my skin, but it looked like it was throbbing as if still hungry for my pussy. He must have seen my face change, or maybe I bit my lip, the moment I saw it because he then made an almost devious looking smile.

"Now you're being a good little sissy pet. It hurts, but deep down you want it again. You've never felt more purpose than when I was inside you. But you've been resisting almost the entire time and I warned you that it'd only make things harder."

I didn't know what to say. Obviously I wanted nothing more than to be untied and let go and for him to leave. But I also couldn't stop staring at his cock. I was never a self destructive person, but something about being used as nothing more than a fuck doll you'd buy at the store was really attracting. Almost as if it was an honor to offer my own body(which I know many guys think is hot) to a beautiful cock so that it can fuck in the way it was meant to. No regard for the other person, all that matters is satisfying cock in any way possible.

Those thoughts flashed quickly though because I still was exhausted, in pain, and wanted this to end immediately. "Please..."

"That's more like it." Purposefully misunderstanding my pathetic pleading. "I bet your pussy hurts after taking a pounding like that for so long."

Now being able to see I caught sight of the clock and realized I'd been taking that brutal fucking for at least 45 minutes straight, which hopefully means this is almost over. Once again he must have seen where I was looking.

"Don't get your hopes up. Daddy's not done training his slave yet. I told you that you better start loving this or it'd be a rough ride, and guess what? That ride is only halfway through."

My heart sank, there is no way I'd be able to survive all of that over again. I didn't even try hiding my expression from him.

"This time Daddy is going to let you watch. I know your little sissy face wants to watch every thrust my cock makes into you. And this time there will be no attitude or I'll make sure this never ends. If you think you're going to beg for mercy, beg for more cock. If you feel like pleading for mercy, plead for my cum instead. If you know what's good for you, you'll be the best sex slave you can. Understood?"

"Yes sir, thank you sir," I said halfheartedly which I'm sure he noticed because immediately he thrust his freshly lined cock back inside me. If the first round felt like eternity, I don't know what word to use to describe this. He pulled my hair back the entire time so that I could watch like he said. Being able to see the clock made time go by even slower than before when it was an abyss of pain, pleasure, and Daddy's cock swirling together.

Not only was my body now being pulled back against him, I was taking a harder fucking as well. Before it was deep and a consistent speed of fucking, but now I could feel my body vibrate with every thrust. That and the look on his face in the mirror, I knew he was fucking me as hard as he could, pounding his cock into my soul. I couldn't stop the whimpers, but I managed to hold back crying out in pain even though that's all I wanted to do. But of course that wasn't good enough. "You don't sound very grateful. Look how lucky you are, I'm letting you take my cock inside you, giving your sissy body a purpose."

So I began giving Daddy what he wanted. Even though I'd never felt pain as bad as this in my life, "Thank you So much, it feels so good."

"I want your cock inside me forever."

"My ass was made for your cock to fill."

"Thank you."

"Please breed my pussy. I want your cum so bad."

This went on for over half an hour. Pulled back against a thick juicy cock pounding me as hard as it can. At first it was all I could do to not say my "lines" with sarcasm or rage. I don't know when it happened, but I eventually heard myself almost moaning my words. Whether he really knew how to train a sissy, or if it was just some new facet of this kink I'd been developing, had I found myself actually enjoying this? I could no longer take my eyes off the small spot, and very brief moment, in the mirror where I could see his cock for a moment before it plunged back into me. I started begging for his cum over and over, both appalled at myself while also wanting nothing more than that. "Please Daddy I need your cum."

"Fill my pussy with your warm load Daddy."

"I've been a good girl Daddy, please."

"Cum in me."

"Please."

"Daddy..."

He musta have really enjoyed that because I could hear his breathing and grunts get more intense. "My slave wants it to be breeding time? Don't worry I planned on impregnating your tight little hole. I'm going to fuck it into you nice and hard, and you better beg the whole time." Daddy went back to pounding away, and I went back to begging.

"Harder Daddy."

"Fuck me deeper."

"Please Daddy fuck me harder."

"Fuck me harder."

"Harder."

"Harder."

"Harder."

Every beg turned Daddy on more and more, and the pain got worse and worse. Tears were streaming down my face as Daddy finally got to the point of slamming his cock into me as hard and fast as he possibly could, but I never stopped. Not because Daddy wanted me to keep begging, but because deep down I wanted to. Looking in the mirror there was no where else I'd rather be. Unable to move, totally helpless, and at the mercy of the cock drilling away at my insides. My body was meant for this exact thing. Firm hands gripping my smooth skin, taking the painful abuse like a good obedient slave, and above all...that cock. Rock hard and pounding a hole to small to contain it, this was my new god and I worshipped it by offering my body in whatever way was desired.

Then my vision went black, my voice muffled, as my face was shoved back down into the bed. I could hear Daddy grunting as he held me down, and pushed his cock as far into me as he could. As he held it there I couldn't help but moan as I felt it throbbing deep inside me, followed by a warm rush as Daddy pumped his load in my pussy. He held it there for a minute, the throbbing slowing down until it stopped after every drop of cum was inside me.

"Good little sluts get rewarded." As soon as he pulled his now limp cock out of me he placed the plug back in. "After I leave I want you to stay like this for a bit while my cum soaks into." I heard him zip his pants and then his footsteps receding down the hall. I could have immediately started working on untying myself and takin out the plug but I laid there like Daddy said. After a short while I realized I didn't even get to cum through the whole ordeal, but I didn't care. The more I replayed the nights events, the less angry I was and the more satisfied I became. At the beginning of the night I thought I bit off way more than I could chew trying to be sissy slut, but that changed. My pussy was offered to a cock like a sacrifice, and I loved every minute of it. Just knowing I was used as a personal cock sleeve was enough, but now I also have an ass full of warm cum. That may have been the first dick I took in this fashion, but it definitely wouldn't be the last.