I May Have Gotten Over Confident

I have a confession to make. I absolutely LOVE blowing straight guys. I always have if I'm honest. I can't help it alright, the devilish plans have been in my mind for years. It started mostly harmless. I'd go to the sex shop or the dive bar and sneak my way into the slutty side of the glory hole and service half a dozen guys on a busy weekend. I know not all of them were strictly straight, but I know some were! The combination of them thinking a beautiful young woman was sucking them off and that masculine musk you only get from straight guys uuuggghhh I can barely contain myself, just thinking about it gets me going. I've literally filled my panties with precum more times than I can count. I've even cum a couple of times when my recipients were fairly verbose. I just love being a sub alright.

Oh where are my manners I'm Jill. I'm in my late 20's and while I've only been transitioning for about 4 years I've been a slutty sub as long as I can remember. My breasts are large b cups, and while I might not be the best looking woman in the bar I'm well beyond passable. Most guys that see me immediately find me attractive if not downright hot. I'm telling you this so you can understand my, shall we say progression.

You see, as with most things, progression is only natural. The less personal nature of the glory hole wasn't the special treat it always was. I remember my first glory hole. My heart was pounding out of my chest, my cock was throbbing with excitement, my mind was scattered and frantic but always came back to the same thought. "I'm finally going to suck a man's cock."

I kneeled in front of that hole and waited. I wanted to play with myself but I didn't want my cummers to hear me stroke my cock. I knew if they heard it the men I really wanted to swallow would run away. I resolved to play when I got home and I could freely stroke until I filled my own mouth just like these men would here. Before I even heard the door across from me my panties had become very wet in the front.

The door swung open then shut quietly. My cock throbbed knowing full well, this was it. Sure enough my first proper man's cock poked slowly through the hole. "Thick" I remember thinking. As soon as I thought that I inhaled his musk. Oh my god I was hooked. I reached for the base of his cock and began kneading slowly. Once he was fully engorged I put my mouth over his head and began working my way to his balls. Hairy and masculine they hung just in front of my chin. I knew I could get him all the way in my throat.

I'd sucked toys bigger than him but this was definitely the biggest cock I'd ever had in my hands. He was a good bit larger than me and the fistful of femboys and random gay men I'd been with up to this point. If I had to guess I'd put him at almost 7 inches, but the girth! Oh that wonderful girth filling my mouth! I reached his balls and aggressively began shoving his cock head in and out of my throat. I wanted his cum more than I wanted air. I heard knocking but I didn't care. I was in the full throws of lust, hell someone could have kicked the door down and all I would have done is say wait your turn. As his cum flooded my throat and my mouth I realized he was trying to tell me he was going to cum. I swallowed what went down my throat and what didn't spilled down my chin and cheeks. I greedily lapped up the stray cum that I had carelessly smeared on my cummers balls. My head swam as the scent of cum filled my nostrils. My cock nagged me by throbbing along with my heart beat. Ugh why can't I just stroke it!

I greedily cleaned my anonymous man's cock. I needed every drop of his cum. My panties were soaked through at this point. My man decided he'd been cleaned enough and removed his cock from the hole. As I was cleaning my face off I heard him say. "Missy, that was the one of the best blowjobs I've ever had, if you want I'll spread the word for you." I started to panic, I didn't want to talk, what if he found out? Would he be angry, turned on, turned off? I didn't have the womanly voice I do these days. Then I had a brain wave.

"Yessssss" I whispered to the other side of the hole. I heard my man reply "Very well Miss, busy night out there, not many women though, I'd bet good money you get plenty of visitors tonight. If I feel like it, I might come back before the end of the night." My brain went mad, I needed a release! Oh my, I could be here for a while huh. My throbbing cock reminded me that it needed attention and when I looked down I noticed not only was I soaked I had actually dripped onto the floor in a few places.

My second cock was pretty plain, he was maybe 4 inches and came in no time. He was a very heavy cummer though! By the time I got the 3rd cock in my mouth I realized I didn't have the resolve to wait until I got home. I had to get some relief! I stealthily stuck my hand in my panties and began squeezing my cock. I still didn't want to stroke my cock, with all the fluids down there it would not be quiet. I was so horny after a handful of good squeezes I shot cum right through my panties, adding to the puddle of precum growing between my knees. My second orgasm waited until after my first cummer returned. I greedily sucked his cock for the half sized load he had left in his balls and I came hard from one quick stroke I timed with one of his. His second load was thick but only had a little volume. No matter, I had two big loads at my knees to clean up before I left. I'm sure I was quite a sight to behold as I slurped and lapped my own cum off the floor. I didn't care, I was lost in my own little world. That first night I sucked 7 cocks and swallowed 10 loads, counting mine of course. I'd grown tired, wet, sweaty, and oh so satisfied. I went into that glory hole an awkward transitioning girl, and I left that glory hole a radiant sexually liberated woman.

And so went my glory hole days. The early days were erotic to my core! Everything was in perfect alignment. My brain was turned on, my cock was throbbing, my lovers were arousing my body with every masculine grunt and moan. It was enough to make a girl cum all on its own! Hell a few times I did! Oh those were the days. However as time went on, I began losing my sense of excitement. Don't get me wrong, it was still a sexual experience but as I gained more experience and it always went so smoothly, the sense of danger and adrenaline just faded. Obviously it wasn't a chore but it started that trend and I needed more.

I had become very passable by my 3rd year of transitioning. I was pretty regularly getting hit on by guys and that gave me the next naughty idea. I had to start wearing compression panties so I wouldn't scare off anyone when I started to get visibly aroused. I spent my first night in the bar getting hit on, having guys grind on my ass, and I managed to pull one guy into the back alley and blow him face to face! Oh what a feeling! He was hot, young and drunk! The nice thing about drunk guys is they get talkative and dirty! He was calling me a dirty girl, cum dumpster, and a whole lot of other stuff that I was loving! I was soooo horny but not being able to touch my cock was agonizing! The throbbing, in those compression panties was soooo good. Being forced to not touch myself while I was swallowing hot straight guy cum was just divine agony! Looking back it was pretty much inevitable that I would cum in my panties.

I had a very busy week, I hadn't had time to sit down, let alone jerk off. Friday night came around and I rolled into a new bar and found a horny man in minutes. In no time at all I had cornered him in the bathroom and just went insane! I slid down him and felt his cock oh it was perfect! I told him "Oooohhh, I am going to love sucking you off!" he looked at me, pulled his cock out and said "I'm sure you will, you're a good little cocksucker aren't you?"

That was all the que I needed. I didn't tease him long, just enough to get him moaning. He clearly had a rough week too, his scent was enthralling, I pulled out all the stops! I forced his cock down my throat and licked his balls. I used my hands to massage his balls and his shaft. I was going to get everything out of him. He looked at me and started calling me sooooo many things.

"God damned, you must have sucked a thousand cocks. You dirty cum dumpster, you're not just good at it you fucking love it don't you? You're probably so wet right now. fuck by the sounds you're making you're either about to cum yourself or you're going to pass out. You are, aren't you? You're such a horny slut that you're going to cum just sucking my cock. Oh fuck, I'm going to cum right down your whore throat!"

He moaned loudly and started throbbing in my throat. He pulled my head down on his cock. His balls smashed into my face. Between him degrading me, being deeply attractive, him treating me like the sexual woman I had become, and now dominating me, using my throat like a Fleshlight my eyes rolled into the back of my head as I felt his cock depositing a massive amount of cum straight into my stomach. I moaned through my nose around his cock, I filled my compression panties completely. I had never cum without being able to touch myself and it felt so damn dirty. Everything he said was true, I was a total cumslut. I was still enjoying my orgasm as he pushed me back off his still hard cock. He saw my O face as I leaned back on my heels. When he saw my face he couldn't help himself.

"Ha, you did cum didn't you! You've got to be the sluttiest girl in the entire state! I've had my share of blowjobs and you're head and shoulders above the crowd. You should give me a call sometime. I'm sure you need a weekly cum top up."

He handed his card to me, put his magnificent cock away and headed back to the bar. I got up, locked the door, and immediately took my panties off to clean them. I stuck his card in the mirror as I licked the massive load out of my panties. I couldn't wait to get home and jerk off. As a naughty reminder of my escapade I left the cum stuck to me right where it was. I put my cum and saliva soaked compression panties on and started the long walk up to my apartment. Every step I took reminded me of my mental orgasm, and fuck did it turn me on feeling the evidence of my depraved adventure slip and slide around under my skirt.

Things went like that for a while, I'd say I blew a dozen or more guys in the next month. It was so wrong and so right at the same time. I know it's a grey area but I'm totally passable and I'm not shaming my cummers or telling them about me. What they see is what they got. I started to view myself as the easter blow bunny. Just hopping along my way handing out blowies to horny straight guys. I couldn't really see anything wrong with it. I still really don't, it's like porn right? Just because it's not exactly what you think it is doesn't mean it's not a good time.

I was just loving my new weekend hobby. I probably could have enjoyed it for months, but one night I got found out. I was hitting on this guy who rode his bike to the bar. He came off soooo straight. Facial hair, tall, tee shirt and shorts, no sense of style. I labeled him as straight the second he came in. He sat next to me and said "What're you drinking miss?" I made up my mind right then that I would blow him.

We chatted for a few hours and he never ordered a drink. He kept refusing my offers saying I have to ride back later. He was into me, categorically. He kept looking at my ass, and down my shirt. I could see he was hard through his shorts. I was probably over confident when I asked if he wanted to go to the alley. He declined the alley but offered to take me to his place. I shouldn't have said yes, but after talking all night and being hammered I just wanted to suck a cock. And hey, I'd always wanted to ride on a motorcycle.

We pulled up to his place and I slid my hands down into his shorts. I loved grabbing his cock, girthy, a good 8 inches. He wasn't a record setter for me but he was just about the perfect size. He gently pulled my hands out of his shorts and led me up the stairs to his apartment. When we got inside we were hot and heavy immediately. I was dying of anticipation. I was salivating over the idea of his cock. He was passionately making out with me, grabbing my ass and calling me a dirty girl. He led me to the bedroom and pulled me onto the bed. I was so turned on I slid down him and pulled his cock out while he laid back on his bed. While I was blowing him he was talking but for whatever reason he wasn't really talking dirty.

"Mmm that's good, you know I've seen you around a bit. I know you are an insatiable slut. I've been waiting for my turn. You see I've admired what you've been doing for everyone and well I figured I'd have my share just a little differently."

As he finished that sentence, I heard some metallic clicking. He handcuffed me! I didn't know what to think. I was thinking huh maybe this could be my new kink. He put the second set of handcuffs on the bedpost. As he did that I realized I wouldn't have much room to blow him! Oh fuck he doesn't want me to blow him! He wants to fuck me! He'll find out! I have to play this off! How the fuck do I play this off?!?!

He looked at me with a wry smile, I had no idea what was going through his mind. I didn't know if he was kidnapping me, or trying to rape me, or if this was just his thing? Hell we all have our kinks, I certainly don't have any room to judge someone for theirs! I looked at him and said "Pretty kinky for a first date don't you think?"

He said "Well, I am a little more familiar with you than your usual first date. I mean, we did work together for a while."

Oh fuck, he knows me outside of the bar. He probably knows my real name! And worse he knows I'm a huge slut! This guy could ruin my entire life here! I can't let him take my panties off! If he wanted to, he could make the rest of my life a living nightmare!

"Well, either way, I really don't do this kind of thing on a first date. Can you just undo the cuffs and I'll go back to blowing you?"

He looked me dead in the face and said "No I don't think so. You see, I know too much. And with what I know, I'm pretty sure I'm going to be able to do anything and everything I want with you."

I was actively panicking now. I couldn't hold it back. I was breathing heavily, I was pretty concerned about what exactly he knew. He was definitely after more than a blowie and while I was a woman I had no pussy to offer him for his silence. I had played with my ass before but not nearly enough to take his cock! Oh why did I say I would go back to his place!!!

He walked around to where I couldn't see him. He started talking again. "You can relax you know, I'm not going to spill any of your secrets as long as I get what I want. And don't worry I know everything. I don't have a problem with it, I don't see any harm done. If anything you're a net positive in the world. Slutty trans woman blows horny pervs seems like a good thing for society. I mean obviously some of the guys probably don't want to see the evidence for it since well, they're straight."

I started to calm down a little, I had to slow down and think. So ok, he knows I'm trans, he knows I love sucking cock, he knows I've blown countless guys in this town and he knows who I am. But he did handcuff me to his bed. Oh no he wants to put his big fucking cock in my practically virgin ass!

"Alright so you know pretty much everything, I do have one thing to tell you that you don't know. I don't do anal, and with how I'm positioned I don't see how I'm going to do anything else."

He responded "Well unless you want these three big straight guys you blew last in my bar last month to find out your little secret, you'll have to make an exception for me."

He hit play on the TV sitting to the left of the bed and there I was. In 4 different angles I was on my knees sucking some guy through a wall. He had a camera pointed up my skirt, one directly down at me, one behind me, and one side on looking down. As if that wasn't bad enough I remembered this session well. The guy behind the wall was a regular, a very talkative regular. I remember my outfit because I shot my load straight into my skirt that day. I left that bar with a huge cum stain in the front of my skirt! It was humiliating! I told someone I was drunk and spilled on myself. I was fixated on the screen. I gotta say, watching my slutty self work that guy over was pretty fucking hot!

"Well I don't think I have much choice in the matter here huh? I'll do it. I'm serious though I don't do anal so you can't just shove that big cock in my ass right away you'll have to go slow mister."

He responded "It's Jeff by the way, and trust me, I know how to stretch out an asshole. Now move your legs forward. I've got more setup to do."

I complied and he rolled my panties down and shoved something small in my ass. I figured out it was a lube nozzle because I felt the lube squirt into my ass. He pulled that out and I felt him slowly work a finger into my tightest hole. I gotta say he did know his way around an ass. He never went too hard and always made sure I was well lubed. He pulled his finger out and slid a small plug into my ass. He pressed a button on it and it started to vibrate. I found it a little unnecessary, like I said I never really enjoyed anal so I thought he was barking up the wrong tree here. He wrapped a strap behind my knees and secured it to the headboard. He wrapped a second one around my waist and secured those to the opposite side of the bed pulling my ass out and my legs together. Then I felt something slide down my cock. I was pretty horny after being tied up and forced to watch me swallow cock for who knows how long. I couldn't help but moan a little bit. I then felt something the size of my forearm get tucked between my legs and behind the strap. I was at a loss. I didn't know what to think.

I said "Ummm, what exactly is that?"

Jeff "It's a wand with a hummingbird attachment."

Jill "Really! I've seen those in porn! They seem really strong, are they as good as they look?"

Jeff "You tell me."

He turned on the wand and immediately I felt a bolt of pleasure shoot through me. I was basically fucking air trying to get all I could out of that thing. I felt him pull the plug out and replace it with a bigger one but I didn't care. I was too distracted to care, this fucking thing was incredible! Like I have to get one of these! I was getting close in no time flat, before I could hit that edge though he turned it off! I groaned with annoyance the second he did it, I wanted to cum soooo bad!

Jill "What the fuck man! I was about to cum!"

Jeff "So? You're tied down, be glad I do anything for you as far as your pleasure. You're filling in for that tonight as far as I'm concerned. You're my fuck toy tonight and I'll do whatever I want with you. Matter of fact, I'm kinda tired of your input."

He cut my compression panties off my legs and shoved them in my mouth! I was a little mad that he ruined my pantie, but I definitely enjoyed the taste of precum in my mouth again. He put a ball gag over my mouth too. well not much I can do now. Being completely controlled by him was very erotic. I was so fucking hard, I'm sure I leaked precum all over his sheets already by now. He flipped the wand back on and swapped my plug again. I don't know how big this one was but it felt pretty damn big. I squealed through my panties a little as it slipped all the way inside my asshole!

The wand was god-damned epic! I couldn't believe how fast it pushed me to the edge. Just as I started breathing heavily he flipped it off again! Uggghhh I groaned through the panty gag again and he laughed. He slapped my ass and called me a needy slut. He wasn't wrong either, I fucking needed to cum! He sat behind me pulling the plug slightly out of me stretching my ass as he did so. I was starting to see why people did anal. It wasn't as good as the wand but I definitely started to enjoy the plug!