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Tier Reward for Anon


After yet another encounter our protagonist finds himself conflicted about whether or not he should turn back into a man. Especially after he sees how hot he looks in feminine clothes.


Previous chapters can be found here!

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My heart thumped against my ribcage. It was probably just my imagination but I was sure I could feel my breasts moving with the intensity of the beat. My fingers were still between my legs, the ache there already growing as if I hadn't cum mere seconds ago. The man from the treadmill sauntered down the stairs with an arrogant smile. I could tell he was the sort of person who was accustomed to getting what he wanted; and right now what he wanted was me. A realisation that sent a shiver of desire down my spine.

Not to mention a wave of humiliation because I wanted him as well. I could deny it out loud as much as I wanted but I knew and more importantly, so did my body. I slipped my fingers from my slit and pressed them against the cool brickwork, swallowing down my nerves. I had to get a hold of myself but that was really hard to do when a very large part of me didn’t want to.

“Interesting outfit.” The man nodded, pointing to my oversized shirt, “Then again, I suppose you're dressed from practicality right now aren't you? Let clothing means less to take off.”

I tried to respond but my mouth was dry, my eyes kept darting down to the bulge in the man’s tight shorts. It was clear he was hard.

“I’m Beau.” He continued, “If we’re doing names, or shall we get right to it?”

“R-right to what?” I shivered, playing dumb my only recourse at this point, at least until I could convince my damn legs to move.

“Don’t be coy.” Beau laughed, “You can't just come right up to me, stare at my junk then get yourself off behind a gym and pretend like you’re not looking for company.”

“Maybe I am.” The words came out before I could stop them and I cringed, I sounded so horny and desperate it even turned me on! No wonder Beau thought this was some sort of game.

He was right in front of me now, reaching out to stroke a stroke hand down my face, cupping my cheek. I shivered; he felt so strong and I couldn’t help but lean into the touch. No matter how much I wanted to, I couldn’t resist him. He was just so close and I was so horny.

I reached out to run my hands over his toned chest, I could feel the definition of his muscled abs even through the slightly sweaty shirt. I’d never had a body so fine when I was a man and I ached with jealousy and desire. I wanted to be him but I also just wanted to have him.

According to that email if I had a man cum in me three times that was it. I would be stuck like this but…one round couldn’t hurt. My curiosity and lust simply could not be ignored; I had to know what it felt like to be properly fucked by this man. After all, Brandon had cum in me, so if this man did as well that would only be twice.

I reached forward, taking his strong jaw in both my now delicate hands and pulling his lips to my own. They were softer than Brandon’s but more insistent and within a second his tongue was pressing against my own. I tilted my head back and let him explore my mouth, the feeling of domination making my skin tingle with excitement as he pressed me back against the wall.

There was something far more primal about this coupling compared to the party. Beau crushed his body against my, squashing my breasts against his chest and his bulge against my mound. It almost felt as through he was trying to merge into me. His hands were rough, but not painful and it gave me the distinct feeling of being claimed.

What’s more, I liked it. No, adored it. I loved feeling all my soft, sensitive womanly parts being touched and teased. It was as if my entire body had become one big G-spot and no matter how or where his fingers brushed I moaned.

Slickness slid down my inner thighs and Beau wasted no time ripping away my shorts. They fell around my ankles and I kicked them away without another thought. Instinctually lifting my leg to wind it around his own. My hands were shaking but somehow they still managed to undo his zipper and pull down his shorts enough to reveal his manhood. Longer, by far, than Brandon’s and just the sight made me squirt a little; something that clearly pleased Beau.

“Please.” I whimpered, my pussy was burning. “Please fuck me.”

“Oh don't you worry, I will.” Beau grinned, “Turn around.”

I obeyed without question, bracing my hands against the wall and spreading my legs wide as Beau lifted my shirt up. The fabric was held at bay by my curvaceous ass and he gave one of the cheek a quick, playful slap before positioning his cock at my entrance. All hesitation gone I pushed my hips back against him, forcing the head inside and moaning when he pulled back.

“Nuh uh, bad girl. I’m in charge here. Got it?”

“Y-yes.” I whimpered. I didn't care what he said or did, so long as it involved pushing that wonderful cock inside me sooner rather than later.

Once I was back in position he thrust. In one smooth movement I went from empty to impaled and the shock knocked all the air from my lungs. There was a short delay as I felt him fill me, then the pleasure came all at once. It was like a bunch to the gut, only pure ecstasy. Beau gripped my hips and began to pull out again before rolling his hips forward once more. He wasn’t taking this slow; he was fucking me raw and it was exhilarating.

With each thrust I felt my moans getting louder despite my best efforts. I’d never had sex this good before and I realised, to my horror and delight, that I couldn’t let this be the final time. I needed this again, I needed more cock, more men, more of this wild, beautiful kind of sex that was only possible with this body.

“Oh y-yeah fuck, babe, I’m getting close.”

“M-me too. But you ahhhh…ahhhh, have to pull out!”

Beau descended into grunts and I knew hje was only seconds away from cumming. It was fine, I would just pull away when I felt he was about to. Any second now, just as soon as I had cum myself. I was so close, so goddamn close. I couldn't stop him yet, not when the pleasure was rising and rising. My pussy began to tighten.

“Yes! Oh yeeeees!”

I was right on the edge, just a few more good thrusts would do it.

“I’m going to-”

“Don’t stop!”

A moment later I felt it, his head hitting my G-spot and I tumbled over the edge, squeezing the shaft buried inside me tight. I wanted to keep it there as long as possible to keep the orgasm going but Beau pulled away, a wet splash landing on my inner walls as he did so. He groaned, finishing against my legs but I still felt the tell tale dribble of something inside my walls.

“Sorry.” he gasped, “I think most of it was on the outside.”

“That’s okay.” I was too busy catching my breath, my hands had been rubbed raw by the brickwork and the slight pain helped my mind to focus.

Had that counted? Had he cum inside me, or did it only count if they fully shot their load? I couldn't be sure. It was hard to care when my body was still being rocked by aftershocks.

“Gotta say babe, you’ve made my day and I still don't even know your name.”

“It doesn't matter. I insisted, the cold reality of what I’d just done washing over me. “Bye.”

I grabbed my shorts and tugged them back on, ignoring the slight dampness they’d developed laying on the floor of the back alley. Beau called after me, wanting my number for later but I ignored him, sighing when he decided not to follow.

My pussy was still burning with satisfaction but how long would that last? Already I wanted to do that again but could I take the risk? Had that counted towards another guy cumming inside me? If it did, one more could mean the difference between the frat like I’d always dreamed of and spending the rest of my existence as a woman. Most disturbing of all, the latter option was sounding better and better each passing moment.

I walked quickly, not sure of my direction. As I passed people on the paths I watched as they snickered, taking in my rumpled appearance and gabby clothes. I felt myself grow self conscious; it was sort of a waste, to have such a lovely body now and hide it under this old shirt.

Without meaning to, I turned into Greek street and as if summoned by the thought my eyes fell on the back yards to one of the sororities. Frilly, girly clothes all hung on the washing line, flapping in the breeze like sirens of silk and cotton. As I gazed at those beautiful pieces, envy washed over me like an unexpected wave. I yearned to possess them, to experience the confidence and allure they seemed to exude. It took only a few moments to rationalise taking a few articles. I was stuck as a woman for at least a few more days. I may as well be comfortable and if I was going to be comfortable, why not hot as well?

I glanced around, making sure nobody was watching, and then quickly snatched a few of the most alluring items from the line. Guilt tingled at the back of my mind, but the thrill of acquiring those clothes overshadowed any rational thoughts. Sorority girls had extensive wardrobes. I was sure they could pass on just a few things.

My fingers closed around a pink tank top and white jean shorts, a pale yellow bra and matching pair or panties, each with a matching bow decal right in the front. I ran, ducking out of the yard and not bothering to look behind me to see if somebody saw me. My mind was focused on getting back to my dorm with my new treasure as quickly as possible.

When I finally arrived a grin was spread across my face. Without hesitation I ripped the baggy male clothing off and tossed them in a pile to be instantly forgotten. The clothing I’d stolen was still slightly damp but I didn't care, slipping my breasts into the cups of the bra felt so right.

Pulling the soft panties against my still warm mound made me sigh in relief; immediately I knew I could never go back to wearing boxers again. Not while I knew how it felt to have my folds so lovingly cupped by the silky fabric of proper panties. The shorts were a tight squeeze, clearly the woman who owned these before me had less junk in the trunk but the extra tightness only accentuated my curves. Same went for the tank top.

I turned to look at myself in the mirror and gasped; the woman staring back at me was breathtaking, her hair, while still short, was feminine, almost like a pixie cut. She oozed confidence that I didn't truly feel and I felt my heart ache; with envy or fear I couldn’t be sure. All I knew is that I was more conflicted than ever.


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