Something New: Edge of Glory
I'd gone home from the club and laid in bed, still wearing the soaked panties and the bra, though I'd taken the rolled socks out on the way home. The feeling of those silky things against my skin and the indulgent feeling had been delicious. Eventually I'd wriggled out of the panties and stroked my cock to an orgasm more intense than any I'd had with my ex-wife. It was when I'd tasted my own cum that the feelings of shame and disgust had begun to set in.
But here I was, a week later, gently running my finger up and down the length of my shaft through the satiny material of the panties, remembering how good I'd felt as Sheila. I'd felt sexy, desired in a way I'd never been before. Sure, it's not like I was special to those guys, but the lust in their eyes the enjoyment that my actions were causing was real enough. Giving in to my desires, I reached into my panties and slowly stroked my cock as I relieved my experiences.
Only this time, as the surging pleasure rose with each movement of my hand, my fantasies didn't stop with drinking the cum from their cocks. It went further, pants coming off, skirt lifting, panties being pulled aside... The orgasm I had as I imagined what came next was one of the best I'd ever had. As I rode the waves, I brought my hand to my mouth, idly licking my cum off of my fingers. That was crazy though, right? I wasn't gay. Was I gay? Here I was in frilly panties getting off to the memory of sucking cocks, and imagining getting my ass fucked. Did it really matter? It's not like it was ever going to happen.
But the thought didn't leave me. All that next week I imagined nothing but big cocks between my lips, hot salty loads on my tongue... and masculine hands on my hips as they fucked my ass like a jackhammer. I knew that I would have to do something about it, so I made my plans. I didn't want anything so elaborate as last time, so I went looking on the shadier side of the internet and found a local glory hole. Maybe if I sucked a few cocks, I could get the other stuff out of my mind.
Friday night, I spent an hour in front of the mirror, primping, applying makeup and making sure my wig was well secured. I tucked my cock down between my legs and pulled a lacy thong on, shivering as the strap rubbed up the crack of my ass. I finished it up with a slinky dress, and out I went. The gloryhole I'd found was attached to an adult shop that had a small video screening room, and all of the comments I'd found said it was discreet but always busy. I was sure to get my fill tonight.
When I arrived, I went to the ladies room, as the messages had said, and sure enough, as soon as I walked in, I heard muffled moans from three of the stalls. I peeked under and saw three sets of legs, kneeling on the ground, but the last stall was empty. I went in, latched the door behind me, and waited nervously. I didn't have to wait very long, as a big black cock was suddenly thrust through the hole in the wall.
I was nervous again, like the first time. I didn't have any lustful college boy eyes to encourage me, and this cock was so much bigger. Nervously, I wrapped my fingers around the shaft, and felt it twitch in response. I stroked it slowly, getting a feel for its size, and knew I wouldn't be able to deepthroat it; I'd need to stroke it while I focused most of my attention on the head. I took a deep breath, feeling the anticipation rise, and leaned in and gave it a tentative lick, right up the slit. It jerked and I heard a guttural groan from the other side of the wall, and that was all it took.
I swirled my tongue around the tip of that big cock, then wrapped my lips around, sealing just behind the head and sucked hard, drawing another groan from my unseen partner. I pushed back as far as I could feeling the thick shaft fill my mouth until the head pushed at the back of my throat, but it wasn't enough. Regretfully, I drew back, keeping the suction on; apparently it was working, because I heard a muttered "fuck" through the wall. I pressed my tongue tightly against the underside of the shaft as I pushed forward again, straining to take as much as I could handle. I was an amateur, but it seemed like this guy had never had such an enthusiastic cocksucking, as it wasn't long before he was thrusting at the wall and grunting rhythmically.
"You gonna cum for me, baby?" I crooned before diving back down onto the huge cock, stroking the shaft, slick with my spit as I sucked as hard as I could. "Cum in my mouth," I begged. "Cum for me, let me swallow it down," I gasped between slurping strokes. The dirty talk must have worked for him, because moments later he surged forward, filling my mouth and making me gag before I felt the spasms and felt the hot cum splash onto the roof of my mouth and cover my tongue. I locked my lips around the head, keeping up the suction and flicking my tongue all over the head as gush after gush of cum filled my mouth. It'd obviously been a while, but I wasn't complaining. Once he'd finally ceased, I let him withdraw, then stuck my cum-soaked tongue through the hole to show him his handiwork before swallowing, and murmuring "thank you."
"Damn," I heard him say. "That was the best dick sucking I've ever had."
"I hope to taste you again," I replied teasingly, but I heard him zipping his pants to go; not tonight, anyway. I wasn't sated yet. I wasn't entirely sure I'd ever be sated, but I knew at least for now I was ready for more cock, and more cum. Luckily, the night was young, and there was already someone taking my big stud's place in the stall on the other side of the wall. I heard the zipper and dropped to my knees again, eyes intent on the hole. The light was blocked, and then another cock was thrust through into my face.
At first I was a bit disappointed. This one wasn't nearly so large as the last, and was even a bit smaller than my college boy or bartender from the club. But it was still a beautiful, eager cock with a slight upward curvature and a thick head. I wasted no time, wrapping my lips around it and immediately beginning to play my tongue all over the head as I slowly worked my way down. I had little trouble getting the whole thing in my mouth, though the big head still gagged me a bit. I must have been a natural cocksucker, because once more my mysterious partner exclaimed in pleasure, and began to thrust his hips, pushing his cock deeper into my waiting mouth. I wrapped my hand around the base and let him fuck my face for a minute before taking control again, bobbing up and down and using lots of tongue.
I heard his quickening breath, and couldn't help but giggle. I let his cock slip out of my mouth with a quiet 'pop', streamers of saliving running from the tip to my lips.
"You like that?" I cooed at him. "You want to cum down my slutty throat?"
"Fuck," he gasped. "Please don't stop!" I obliged, sucking him back into my mouth, swirling my tongue around the head before engulfing it fully, then back out until my lips slipped over the edges of the head. I could taste the sticky-salt of his precum, and lapped up the slit before sliding back down the length of his shaft once more. I hummed as I felt the head of his cock bump the back of my throat again, and with only a quick stiffening as warning, he began to fill my throat with hot, sticky cum. I swallowed it down to avoid gagging, but it just kept spurting, filling my mouth until I couldn't handle anymore and I withdrew, letting it drip down my chin. I caught one last splash across my lips, then lapped the remnants oozing from the slit before he withdrew from the hole. Once again, I leaned in so he could see my cum-spattered lips and and swallowed the last bits, scooping a dribble into my mouth and sucking it off my finger.
"So much cum," I said. "Delicious!" He didn't answer, but withdrew quickly. I felt a little disappointed; I obviously wasn't here for a relationship, but I appreciated feedback that let me know that I was a good little cocksucker. No matter; another man was already taking his place, and I definitely wasn't done yet. When the next cock was thrust through the hole, I didn't play coy or hesitate; it was bumping my throat so fast that all I got from the other side of the wall was a gasp.
I was so eager for another mouthful of cum that I lost track of everything else. I should have been aware when I heard someone else walk into the bathroom, but my focus was on seeing how deep I could go on that beautiful dick. I was peripherally aware when the door rattled behind me, but I could feel the twitching that precedes a good load, so I kept going. It wasn't until a hand pulled my dress up and I felt a hand on my ass that I really realized I wasn't alone in my stall anymore. I was so shocked that I didn't know what to do for several long seconds, and reflexively just kept bobbing on the cock in front of me while my brain processed what was happening. The hands on my ass obviously took this for consent, as thumbs hooked into my frilly panties and started to pull them down.
"Wait," I gasped, letting the marvelous dick slip from between my lips. I didn't know what to say, but I knew I didn't want to be discovered as a crossdresser. In a place like this, this was probably pretty much expected, so unless I was willing to cut and run- which I wasn't, since I still hadn't drained the cum from the cock in front of me- I had to find a way to go along with it without blowing my cover. Feeling a wave of fear and excitement, I reached back, slipped a finger into the strap of my thong, and pulled it aside, baring my asshole to my unexpected visitor.
I don't know what to expect, but I was ready to see it through, just to avoid getting caught, quite literally, with my pants down. Nothing happened for a moment, so I distracted myself by returning my attentions to the neglected cock, slipping my lips over the head and running my tongue up and down the slit. After what felt like forever, the hands on my ass adjusted to pull my cheeks wider, and I tensed, bracing myself for what was to come; but what came wasn't what I expected. Instead of the insistent head of a cock, I felt something warm and wet slide over my asshole, and I jumped at the surprisingly pleasurable feeling. I chanced a glance back, and I saw the top of a head, the face obscured under my skirt and felt his tongue swipe across my puckered hole again, and I knew I was lost. Right here and right now, there was nothing more I wanted than for this moment to last forever. I bobbed deep on the cock, gagging as my surprise lover thrust his tongue into my asshole, rapidly several times. I moaned, and that seemed to send the cock in my mouth over the edge as it jerked and shot a big load all over my tongue. I was too distracted by what was going on behind me, so I just swallowed as the cock was withdrawn, and another took its place.
I went to town on the new cock, and the tongue, with one final teasing lap, withdrew completely, and was replaced by something much thicker. Surprisingly, he was gentle, teasing it up and down my asscrack, occasionally stopping to nudge at my asshole.
"Tell me you want this," I heard him say, the head pressed firmly against me. I pulled the cock out of my mouth with a gasp.
"Oh, please," I begged, not hesitant in the slightest anymore. I was done being half of a woman. "Please, fuck me."
"Say you want it in your ass," he said, thrusting just a bit, drawing another gasp.
"Yes!" I shouted, pushing back, the discomfort of his head stretching my hole nothing beside the yearning to be filled. "Please fuck me in the ass!" And he did. He pushed in slowly, and I gasped as my asshole stretched around his thick, bulbous head. It was painful, but as I willed myself to relax, I felt the pain fade a little into the background. I noticed the cock had been withdrawn, but I caught glimpses of a fist stroking it from the other side of the hole; neglected as he was, the sound of my virgin ass getting spread was enough to keep his attention. I leaned forward, putting my mouth right up to the glory hole, and he gave me what I craved, shoving his cock back through and between my eager lips.
The next few minutes were a blur, as I tried to focus on the lovely cut cock pushing at the back of my throat, while unavoidably attentive to the thick shaft splitting my asshole. He was gentle, drawing it out slowly and pushing it in just as slowly; that was the part I liked best, especially once it was all the way in, and I could feel his balls slapping against my butt. I felt so fulfilled, so complete. I'd known before I'd come here tonight that I could never go back to the life I'd known before, but now I knew that this was who I was; a cockslut, and I loved it.
My attentions on the cock in my mouth soon paid dividends, and I swallowed another load, and my unseen lover from behind began to quicken his rhythm, until his balls were slapping my ass in a rapid tattoo. Inside my panties, my own cock was oozing with precum and I could feel it running down my inner thighs, somehow completing the absolutely nasty joy of the moment. Another cock filled the glory hole and I went to work, wondering if I would soon have a hot, creamy load in both of my holes at the same time, and shivering with delight at the thought.
Despite the intensity of the experience, or perhaps because of it, I couldn't help but think about the chain of events that had led me to this filthy, amazing moment; dressed in the sluttiest dress I could find, on my hands and knees in a gloryhole in a skeezy adult store, with one cock in my mouth, three loads of cum already down, and another cock pistoning my previously virginal asshole like a machine. The frigid bitch of an ex-wife, the silly ideas brought on by Jack Daniels, the primping, the college stud and the bartender... It all made perfect sense when you looked at it from hindsight, and I'd never been happier.
My unseen lover was really getting into it now. His hands were tight on my hips as he hammered hard and fast into me, and I felt something that I'd never felt before; despite the fact that no one was touching my own dick, still straining at the silky prison of my panties, an orgasm was building, and it was going to be a big one.
"Don't stop," I begged around my mouthful of cock. "Please, don't stop." I don't know if he understood me or even cared, but it seemed as though his pace quickened even further and his thrusts pushed even deeper until finally his hips jerked and he slammed harder into my asshole than before, pushing my face forward and the cock down my throat. I could almost feel the heat of his cum emptying into my ass, and I definitely felt the thick head of his cock throb with each pulse. It was just enough to drive me over the edge and I felt my own cock twitching in its confines, and pulses of cum fill my already drenched panties. I groaned, barely able to breath with the cock pushed deep in my throat. Luckily, I didn't have to do much more as that cock too began to twitch and spurt cum down my throat until I gagged and withdrew, for once not swallowing the mouthful, just letting it drip from my lips as I slumped to the floor.
I felt my mysterious partner pull his softening cock from my asshole, leaving it feeling empty and well-used. I heard both of them zipping up and chanced a glance behind me. The man was tall and in the afterglow of the serious fucking I'd just received, I honestly couldn't make out his face. He glanced down at me and I caught the impression of a smile as he pulled a small wad of cash out of his wallet and tossed it to the ground.
"Hope to see you again," he said before turning away and walking out the door. I heard rather than saw another cock thrust through the gloryhole, but I was too spent to do any more; after a few moments, it withdrew and was not replaced by another. Eventually I came back fully to my senses and did my best to collect myself. I pulled my skirt down and smoothed it over my hips, straightened my wig by feel, and stepped out of the stall; I hesitated only a moment before ducking back in to grab the cash my surprise visitor had left me. The stall next to mine was occupied, and by the sounds of things the girl was doing her best, but didn't seem to have the same gusto that I'd felt. I checked my makeup in the mirror and was only slightly dismayed to see that it was a complete wreckage. I couldn't help but smile as I remembered why that was. I adjusted my wig again and raised my head before walking out of the lady's room looking and feeling like exactly what I was; a cockslut and an anal whore.
This had been a night of firsts, but I knew that it was far from the last. I'd found my 'something new' and I wasn't ever going to go back to the life I'd known before.
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