A Sissy Tale

It was my 18th birthday. I sat in my dingy room, naked and deeply reclined in my computer chair, with my stiff cock still twitching and spasming in my hand. I had just finished jerking off, the fresh load of warm cum splattered across my stomach and chest, and I caught sight of myself in my mirror.

I really do kinda look like a girl, I thought. I stood up. I'd always been a skinny guy. My skin pale, my body close to hairless, my features delicate. I noticed a curve in my hips... when did that get there? Even my chest, sticky with my own cum, looked soft and feminine. I had been taking pills every day, I was told they were testosterone boosters, and I would notice my pecs starting to grow. My chest was definitely growing but the two soft, budding orbs, no bigger than the palm of hand, sure didn't look like masculine pecs to me.

Little did I know, that would be the last time in my life that I jerked off alone. The last time I had an orgasm without getting permission first. As I felt the viscous goo of my own semen congeal and I reached for an old t-shirt to clean up, I was clueless to the fact that this would be the last time wasn't consumed...

I cleaned up, got dressed, and ready to head out to a party. No, not a birthday party for me. I didn't have enough friends to have a birthday party. I didn't really have any friends at all. I was only going to the party because I was invited by Shane.

Shane was 22, a senior at the local college, and a stud hockey player. I was hardly a stud anything and still a senior in high school, although honestly I was probably going to drop out. Shane had befriended me about six months ago. He and his buddies would come into the crappy fast food joint I worked at and for whatever reason he seemed to like me. We started to hang out and I'll admit, I kind of followed Shane around like a puppy. I didn't have many other friends, he was older and cool in every way, girls seemed to gravitate to him, and simply put he was the guy I wished I could be.

So of course, I didn't bat an eye when he started making suggestions on what clothes I wore, or how I did my hair, or anything like that. Nothing was out of the ordinary, and if Shane thought it was cool then I was all in. He gave me the daily pills, alleged testosterone boosting miracle drug that was anything but, and I hoped and prayed that any of his confident, masculine, macho charisma and confidence might just rub off on me. If I could pull just one girl half as hot as the ones he turned down, I would be in heaven.

The party was just your typical college kegger. Shane and all his jock buddies and whatever girls they could invite. I'd gotten to know most of his friends over the past few months but I didn't fit in with them. They definitely picked on me a bit, most of it good natured but if any of it got out of hand Shane always came to my defense. The party itself was pretty uneventful, it's what happened the next morning that changed my life.

I blacked out during the party. Really, sloppy drunk. Shane's friends kept feeding me shots and I wanted to be as cool as them. I woke up with a searing headache and as soon as I moved, I felt something strange. Unfamiliar. Hard plastic. Between my legs. I stumbled into the bathroom at whoever's apartment this was and was shocked to discover that my dick and balls had been stuffed into a tiny plastic cage. It was locked, and I definitely didn't have the key.

I stumbled out of the bathroom and tried to compose myself. I looked around. There were a few bedrooms doors, all closed, and I'm assuming whatever roommate occupied that room was in there with whatever chick he had picked up at the party. Thankfully I found Shane passed out on one of the couches in the big open living room.

Shane was wearing only his boxers and was crashed on the couch, his legs splayed wide apart and his muscular chest heaving gently as he slept. I went to wake him but froze. Shane's morning wood tented his boxers and it was immediately obvious that he was hung. Of course he was. I felt a tinge of jealousy. I wasn't particularly small myself, in fact I'd watched enough porn over the years to know that I had a good size dick, but mine could never make a tent that big.

I felt an ache between my legs and became immediately aware that my own morning wood was restricted, forced to stay locked and limp, and I noticed the beginnings of an ache not too dissimilar to blue balls. What the fuck.

"Shane... Shane, wake up," I whispered. He stirred, clearly he had drank quite a bit himself last night, and shifted positions but didn't wake up. In the process his hand fell and sleepy grasped his massive erection, rubbing himself gently through his boxers as he settled. Fuck. Even Shane's hand, which was the big mitt of a 6'4" hockey player, looked small as it wrapped around the monster hidden beneath one thin layer of fabric.

"Hey Shelley," a voice behind me said. It was Jason, one of Shane's friends, making his way into the kitchen. "How's the fit?"

I looked back at him quizzically but didn't reply, not grasping his question, as Shane started to rouse. My name is Michael, but all of Shane's friends have begun teasingly calling me Shelley. Short for Michelle. Assholes.

"What's going on?" Shane said groggily as he came to and sat up, oblivious to his massive erection now pointing right at me.

"Somebody... um... well, one of your friends... um..." I stammered, suddenly embarrassed and unsure how to explain the tiny pink cage around my package.

"Somebody fuckin' with you again?" Shane asked with genuine concern. Or so I thought. I nodded and blushed.

"Hey Jay, man, somebody messin' with Michael again?" Shane asked as Jason returned.

"Wasn't me," Jason said with a shit-eating grin that we all saw right through.

"C'mon bro, what'd you do?" Shane asked. Jason just smirked and held up a tiny pink key. "Oh shit!" Shane said, immediately recognizing what it meant, and burst out laughing. He saw that I wasn't laughing and composed himself. "Okay, man, very funny. Give me the key." I noticed Shane said to give him the key, not to give it to me.

Jason frowned. "Why should I?"

"Cause it's not cool, man," Shane argued, though he still carried a hint of a smile.

"What are you gonna give me for it?" Jason asked.

Shane frowned. "Well, what do you want?"

Jason looked pensive for a moment. "Well... slut I hooked up with last night bailed and left me with a raging case of blue balls man..."

"And..." Shane raised an eyebrow.

"And... if little Shelley here helps me out, I'll give you the key."

"Excuse me?" I said, stunned.

"That's fucked up, dude," Shane said.

"Have it your way," Jason said, dropping the key into the pocket of his shorts. "Have fun going to the hospital or wherever to get that thing off," he said with a laugh.

"Wait, wait, wait," Shane held up his hand to Jason and then looked at me. "Michael?"

"What???"

"It's just a little blowjob," Jason said with a chuckle as he grabbed at his crotch.

"What the fuck?"

"I mean, what could it be, like five minutes? Ten tops? Then he'll give me the key," Shane said with a shrug. "That, or I take you to the hospital or I don't even know where..."

"C'mon Shelley," Jason said as he shuffled around and took a seat on the other end of the couch, "I won't tell anybody." He was already opening his fly, as if it was just a foregone conclusion.

Shane gave me a shrug. "It's okay..." he said, trying to reassure me.

I don't know how long I paused, it all felt like some kind of blur, but soon I was on my knees in front of Jason as he pushed his shorts and boxers down. I took his soft cock into my hand gingerly. It felt strange, a fleshy warm tube that was different than my own. It was smooth and decently long even flaccid, with a smooth pink head that ended in a pronounced pointy tip. I closed my eyes and lowered my mouth towards it, hoping this would all be over quickly.

"Oh yeah, atta girl, suck my dick," Jason growled as it neared my lips. What the hell was happening? I got the scent of him in my nose, day-old sweat, and as I slid his smooth head past my lips the first taste was wet and sour. I think he had just taken a piss. God, this was disgusting.

"Mmmmmm," I moaned. Why the fuck did I do that? A held Jason's head in my mouth, a little unsure how to proceed, and let my tongue roll over him as I contemplated my next move. I'd seen enough porn to know how different blowjobs looked - slow and worshipful, deep and aggressive, lots of licking and kissing, vacuumed-sealed sucking - but I had no idea how to actually do any of it. I never in a million years thought I would have a cock in my mouth.

"Fuck yeah," Jason groaned as I felt his cock stiffen in my hand. I noticed I had started bobbing gently, still just on his head, but clearly he was enjoying it given how quickly he was getting hard. I decided I was not at all ready to try to push any deeper on Jason, both because of my own lack of skill and because I wasn't exactly happy about having to give this asshole any pleasure. But I also wanted this nightmare to end as quickly as possible. So, I decided to keep my lips sealed and focus on his head, knowing all the sensitive areas, and see if some gentle bobbing rhythm combined with strong licks from my tongue was enough to get this over with.

"Oh fuck," Jason moaned and his whole body shivered. He threw his head back and put one hand on the back of mine, which I didn't love. But he simply held it there, he didn't push or take charge, so I guess that's just how guys like to have their dick sucked. A few minutes passed like this: Jason moaning and mumbling swears under his breath as I sucked, licked, and moaned around the sensitive head of his rigid cock. Why was I moaning so much?

"Damn..." I heard Shane mutter. Shit, I had almost forgotten he was watching. "How's she doing?"

She? She!?!?! I was used to Shane's asshole friends teasing me for my relative lack of masculinity but I thought Shane had my back?

I felt my dick, flaccid and sadly locked, flex against its constraints. What the fuck?

"Fuck dude," Jason groaned, "she's gonna suck the fuckin' soul outta me! I think she really wants this cum!"

"Fuck..." Shane growled.

I felt Jason's hand grip my short hair firmly. "Yeah you do, don't you baby? You want this fuckin' cum?" I looked up and made eye contact with him for the first time. Jason was always kind of a goofy shithead, but now there was this primal, animalistic hunger in his eyes. I'd never seen him that way before. I felt a tight tension in my balls, the same ache I had felt when I had seen Shane's massive morning erection a few minutes earlier.

I was so focused on the task at hand, on the crazy truth that I somehow had this asshole's cock in mouth, that I hadn't even considered what happened next. What would I do when he came? Pull back and let him blow? Take it in the mouth and then spit it out? A new tangy, slightly salty flavor - a trickle of pre-cum - let me know that it was time to decide.

Suddenly Jason sat up, let out a loud bellow, and gripped my head firmly with both hands. "Fuuuuuck!!!" he hollered, surely loud enough to wake the household, as I felt his shaft spasm in my hand and his cock erupt in my mouth. A hot blast splattered the roof of my mouth, quickly dropping onto my tongue as the next shot followed. I tried to recoil but Jason's grip was firm.

"Fuck! Yeah, oh fuck yeah bitch, take my fuckin' cum!" he berated me as burst after hot burst coated my helpless tongue.

It tasted... awful. I'll be honest. I was repulsed. I'd never sampled my own and had only heard that it was slimy and salty, which were both true, but I wasn't prepared for the sour tang that suddenly overwhelmed my senses. I felt my balls tighten and my cock flex pathetically against the tight cage. What the actual fuck?

"Fuck yeah," I heard Shane grunt as he watched, a noticeable hunger in his voice.

A moment later it was over. Jason flopped back onto the couch and let out a deep, satisfied sigh. I gently let his cock out of my mouth, most of his hot mass still in my mouth but a few slimy strings of spunk clung from my lips to his satisfied cock, and I sat back on my heels.

"Fuck yeah baby," Jason said in a happy, satisfied tone. Like I was his girlfriend or something. Unsure what to do and with a mouthful of sour slime, I put my hand up to my mouth and started to carefully expel the hot load into my palm. "Oh... what do you think you're doing?" Jason snapped.

"Oh c'mon, you got what you wanted," Shane said.

"No way," Jason shook his head, "you know it doesn't count unless she swallows."

Shane glared at him for a moment and then just kind of shrugged. "Yeah, I guess that's true." They both turned to look at me.

"Are you serious?" I asked as a pool of spit and cum swam in my palm.

"Go on baby, suck down all my cum. You know you want to," Jason smirked, back to his snarky shithead self.

"Fuck you," I growled.

"Fine," he shrugged and looked at Shane, "guess you're not getting that key." There was a long pause as they waited for my next move.

"Fuckin' asshole," I said as I took the slimy goo back into my mouth. It had started to cool and was twice as disgusting now as it had been minutes before when it was first shot into my mouth. I retched and gagged as I tried to gulp it down. I could feel the gooey mass cling to every inch of my throat as it slid down into my empty stomach. Nauseating. My balls clenched again I heard myself moan.

"Yeah, there's more where that came from baby," Jason said with a grin as he gave his spent but still swollen cock a few playful strokes in my direction.

We were all speechless for a few moments. I noticed Shane's boxers were still obviously tented. Then we heard some commotion as others in the house were obviously waking up.

"We should get out of here," Shane said as he found his clothes. Jason tucked his satisfied cock away and got up to leave.

"Aren't you forgetting something?" I said, holding out my hand for the key.

"Oh, of course," he said, pulling it from his pocket and dangling it just above my palm. I swiped for it and he pulled it away, laughing derisively as he did, and handed it to Shane instead. I expected Shane to hand it to me but watched it disappear into his pocket instead.

"C'mon, let's get out of here before any of these other assholes wake up," he said to me, putting his hand on the small of my back and guiding me toward the door.

"Don't be a stranger, Shelley," Jason called after us as we left.