The following tale of sexual depravity contains adult material. If you are under the legal age for your area (generally 18 or 21), or object to explicit sex, stop reading NOW. Otherwise, if erotic situations and taboo acts turn you on, then please enjoy yourself. The characters and situations are, of course, completely fictitious.
Feel free to post or archive, as long as the story remains intact and unmodified, and my contact information is attached. Otherwise, this work should be considered copyright 2011 Sissy Princess Heathyr.
A Sissy (S)exercise Fantasy
by Sissy Princess Heathyr sissyprincessheathyr@gmail.com
I stopped going to the gym about six months ago, when money got tight and I had to find ways to reduce my expenses. I usually don't get to the gym much in the spring or summer months anyway, so it was an easy expense to cut. I hate going into the office all sweaty, so I avoid working out in the mornings, and the last thing I want to do at the end of a day is trade one dark, windowless space for another.
Of course, as the holiday weekend passed and the summer heat began to beat down, I found the lack of exercise taking its toll on me. I wasn't at all happy about how I looked or how I felt, and I'm talking generally, not from a gender/sexuality perspective. I kept making plans to start exercising again, to get outside and do something in the morning, when I could count on having time to come home, relax, cool down, and shower before driving to work in air-conditioned comfort.
It didn't work. Every week I would make plans, and every morning I would find an excuse not to get out. I just couldn't find the motivation.
Ironically, it was during a quick trip to Wal-Mart to grab some comfort munchies -- Doritos, Cheese Sticks, and Rainbow Chips Ahoy -- that I finally figured out what the problem was. I was walking by the women's clothes when I spotted the cutest black-and-pink workout set. It sang out to my sissy heart, called me away from the snacks I didn't really need anyway, and demanded that I submit to its Lycra embrace.
Without a moment's hesitation, I walked over and began rifling through the racks, looking for my size. I won't lie and say I'm a perfect sissy size six, but I seem to be about average, and never have an issue finding something cute in my size. There were lots of other cute color combinations, and I thought about getting a different outfit for every day of the week, but the empty spot in my wallet convinced me that two would be enough. The outfit that had originally called to me featured a pair of black shorts, with an inch-wide pink strip up the left side, and a pink top with a three-inch wide band of black running just below the breasts. The second outfit I picked up was the mirror image of the first, with predominantly pink shorts and black top.
I quickly grabbed a couple pair of white ankle socks with tiny little pink pompoms on the back, and then headed directly for the shoes. As I sat there trying on women's running shoes, gleefully ignoring the disapproving looks of the blue-smocked old bag who kept haunting the aisle, I found a renewed sense of purpose washing over me.
The reason I hadn't been able to motivate myself to exercise, I realized, was that I really didn't care how I looked as a man. In fact, I wanted nothing more than to forget that image, and to never see myself like that again. That was hardly a revelation to me, but realizing how desperately I wanted to look good as a woman, or even as a sissy, I began to understand the strange dichotomy. Even though the man who trudged into work every day shared the same body as the sissy who pranced around the house every night, they really were two different people. I couldn't get motivated to make him look any better, but I was super motivated to make her look good.
There was a pair of pink canvas sneakers that I absolutely, but they offered no support for running, no matter how much I tried to convince myself otherwise. In the end, I settled on a pair of plain white leather running shoes, but bought myself a pair of bright pink laces to put in them.
On my way to the checkout I picked up a bag of pink and purple scrunchies for my hair, along with some baby-powder scented antiperspirant. I already had a few padded panty girdles at home, to provide some definition while flattening out my sissy bulge, along with some padded sports bras that would fill out the Lycra shirt nicely. The watch I wore everyday was a thin, purple girls sports watch anyway, so my workout outfit was complete.
Sure enough, when the alarm went off the next morning, I was up and out of bed in a heartbeat. I was excited about exercising again, and determined to start developing the kind of sissy curves I would need to land myself a real man -- preferably one who would take me away from it all, trading my tie for a studded leather collar, but I'd just as happily settle for one who would fuck me silly and leave me leaking cum.
As I dressed, I felt my entire personality change. It was a transformation that usually only came over me after work, when I traded dress shirts for blouses and pants for skirts, but one that I hadn't felt so strongly since the first time I had Nair'd myself hairless in the shower -- and then lovingly caressed my wondrous, impossibly smooth legs until the water ran cold.
Before I could look in the mirror and spoil the illusion, I opened the treasure box atop my dresser and pulled out my new glasses. Thanks to my allergies, I'd never been able to wear contact lenses, so I usually had to prance around blind, rather than let my black, boring, boy's glasses ruin my carefully constructed façade of femininity. Thanks to the miracles of online shopping, and a great summer discount I'd stumbled upon, I finally had a pair of prescription glasses that I could happily wear while dressed as my soul demanded.
The frames were much thicker than my normal glasses, but the plastic was a shiny purple, with tiny diamond-like sparkles all over. The lenses themselves were just over half the size I was used to, but nicely shaped, with almost a retro cat's eye look to them.
They were perfect. I slipped them on and smiled at the pretty sissy in the mirror. We were perfect.
My plan was to ride my bike across town to the public track, run (or at least jog) a full mile around it, and then bike home. I estimated that would give me a solid hour of exercise, and would definitely work up a sweat. I felt a little self conscious about being so publicly exposed as a sissy, but I knew traffic would be light at five o'clock in the morning, and the only other people on the track would be serious joggers who wouldn't care about anything but their time.
Finding two nearly-flat tires on my bike didn't exactly get me off to the best of starts, but the gas station was only a few blocks away, and only a little bit out of my way. I struggled up the hill to get there, fighting gravity as much as the slack tires, but I looked at it as added exercise. Fortunately, I'd thought to pack some change in my fanny pack along with my house keys, so I was in good shape. I popped my fifty cents into the machine and quickly set to filling my tires.
While I was doing that, a big-ass pickup truck backed into the space next to. The driver made me a little nervous, especially when he climbed down out of the cab, but he just smiled and waited patiently. When I was done, he asked if he could have it, and even handed me a quarter to split the cost. His tone was so warm and so polite, I wondered for a moment if he might be the man to fuck me silly, but when I thanked him for the change, his whole demeanour changed.
I took the hint and quickly got on my bike. As I pedaled away from the pump, I heard him mutter, "Fucking sissy faggot. Oughta be forced to wear a sign, I tell ya."
Suddenly, the flat tire was the best part of my morning. Sure, it may not have been meant as a compliment, but he'd just validated my sissy femininity in a way that no mirror ever could. I was tempted to ride back and blow him a thank-you kiss, but I knew that would be pressing my luck.
I had a moment of fear as I pulled out of the gas station and saw a police SUV turn the corner behind me, but he passed me by without incident. I wasn't wearing a helmet, and the light on my bike had needed fresh batteries for over a year. Neither was enough to get me a ticket, but I'd had a few stern warnings over the years, and I didn't feel like putting an end to my morning exercise for something so boring as a lecture quite so quickly.
When I finally pulled into the park, my chest was sore, my legs were rubbery, and I was completely out-of-breath. Clearly, I was in worse shape than I thought. I spotted a police SUV parked in the church parking lot across the street, and idly wondered if it was the same one that had passed me earlier, but didn't think much of it. The cops were always parked there, and I felt a little better knowing there were watching eyes to protect me in case some macho runners decided to take offense to sharing the track with an effeminate sissy.
That was assuming, of course, he was the kind of cop to give a damn, instead of turning a blind eye to a little pride-bashing.
What I had planned to be a run quickly became a jog instead, and even that didn't go well. I was on my second lap, coming up to the half-mile mark, when I hit the wall. If I'd been driving, I might have pushed through it for another lap, but I knew I still had a half hour ride home ahead of me. So, a little disappointed in myself, but more determined than ever to get back in shape, I finished the lap and headed for my bike.
As I took a long sip of water from my bottle, I realized I was a sweaty, trembling mess, but I was a sweaty, trembling, sissy mess, and that made all the difference. I was quite proud of myself, and eager to do this again tomorrow. Finding my second wind, I hopped on my bike and rode out of the park, and into the street.
That's when the cop flashed his lights at me and waved me over.
Crap.
Hoping to make it quick, I checked for traffic, and then rode across the road and into the church parking lot. As I approached the SUV, however, he began backing up, still waving me forward. He only stopped when he was against the back fence, beneath the shadows of the trees overhead. It was a little creepy there, right next to the graveyard, and definitely more secluded than I felt comfortable with. All I could do was hope that somebody had seen me heading out from the track.
"Good morning, officer." I tried to see some glimmer of emotion behind the mirrored sunglasses, but he was giving nothing away.
"Park your bike by the fence, and then get in." He pointed to the passenger side door to emphasize the point.
The rational, cautious, masculine side of my brain was screaming for me to run. It told me what a bad idea this was, and chastised me for being so stupid as to even consider getting inside that SUV with a power-tripping cop. The sissy side of my brain, however, told it to shut the fuck up and watch.
The moment I slipped inside, he raised the windows and locked the doors. I was scared, but it was a good kind of scared . . . the kind that makes your panties wet with pre-cum!
"You look like you've had quite the workout." He smiled at me and removed his glasses. He had the most amazing blue eyes, bright and piercing. They were the kind of eyes that could just as easily sweat a confession out of somebody as seduce one. "My, but you are sweaty! You look like you're about ready to drop from exhaustion."
I nodded, afraid to do otherwise. "Yes, sir."
"What do you have to drink in that bottle of yours?"
"Just water, sir."
"Just water?" He shook his head softly. "You should know better than that. If you're going to be working yourself so hard, then you need to inject a little protein into that body." He laid his hand on my thigh, just high enough that his pinkie finger was brushing the tip of my cock. I felt a jolt of electricity shoot through my body at his touch, and it had nothing to do with the Taser on his belt! "Really, if you want to maximize your recovery, you should be sucking down something a little more . . . solid."
I couldn't believe this was happening! It was so wrong, so inappropriate, and so completely my fantasy. Here I was, locked in a well-insulated SUV, with a cop who had, no doubt, a solid explanation and alibi already prepared to explain my presence, should things go wrong. He was so totally coming on to me! The only question was whether he knew I was a sissy, or whether he thought he was chatting up an awkward young woman.
"Every woman can use a protein shot once in a while but, to be truly happy and healthy, a sissy girl should ensure he has at least one daily." He fixed me in place with a knowing wink.
Bingo! With things suddenly clear between us, I felt my cock growing beneath his touch. "Yes, sir." I licked my lips seductively. "Not that you mention it, I am rather thirsty, sir. A good shot of protein might just do wonders for me."
Suddenly, I felt the chair lower itself beneath me, even as it slid back a few inches. He let go of the adjustment buttons and smiled. "There's not as much room as there'd be in a stock SUV, but I think you'll find enough room to get down and comfortable on the floor.
He was right. I slipped off the seat and knelt quite comfortably on the floor. I had to crouch to keep myself beneath the dashboard, but since that brought me closer to his crotch, I don't think either of us had an issue with that.
I watched, mesmerized, as he began stroking himself through his police blues. I could see his cock swelling beneath the zipper, and felt myself beginning to lean forward. As I reached out, he took his hands away, giving me full access. I all but ripped the belt off of him, but then took my time unzipping his pants. The last thing I wanted, at that point, was to catch his skin and have him toss me out of the SUV, horny, bruised, and completely unsatisfied.
The moment the zipper reached the end of its journey, his white briefs began straining upwards towards me. I'd never been quite so forward before, but something compelled me to lean over and nibbled his shaft through the cotton, inhaling the overwhelming scent of musk and sweat as I did so. Clearly, judging by the smell, he was near the end of a long shift, but the more he smelled like a man, the more I wanted to do this for him.
Suddenly, I felt a gentle cuff upside my head. "Maybe another time, sissy, but we're a little pressed for time here." He lifted his ass off the seat and helped me pull the pants and briefs away from his cock. "Get sucking."
Oh my god, it was glorious! I'd sucked longer cocks before, but never one quite that thick. I wasn't even sure I'd be able to get it in my mouth, but I knew I'd make the effort -- and then some! The moment I lowered my face to his cock he grabbed the back of my head, pulled me close, and thrust his hips up towards me at the same time. Before I could even take a breath, I had five inches of thick, hard, cop-cock buried in the back of my throat.
My jaws hurt, and I felt like I was going to gag. It was the most glorious feeling in the world.
He was too thick to really suck the way I'd like, so I settled for licking and slobbering all over his shaft, while he held me in place and fucked my face. He was a demanding lover, and one who knew what he wanted -- and just how to get it -- but he wasn't careless. His thrusts in and out of my mouth were well-placed and well-timed, allowing me just enough time to breathe between mouthfuls of cock, and never pressing too hard or too fast into my throat.
It wasn't long before he was moaning softly. "Good girl."
Those two words filled me with such a sense of sissy pride that I came in my panties. He must have felt it, because he quickly shoved his hand beneath my shorts and caressed me with his callused palm. It felt good, but I was so sensitive from coming, I cried out and tried to pull away. Of course, I couldn't really go anywhere, impaled on his cock as I was, but the effort was there.
When he pulled his cock all the way out of my mouth, I wanted to cry. I immediately lunged forward, only to be snapped back by the hand in my hair. The pain brought tears to my eyes, but what he did next made it all worth it.
"Sissy protein isn't nearly enough to maximize your recovery, but it might be interesting to see what it does for your performance." He began stroking his cock, smearing my spent cum all over it, until it glistened in the early morning sunlight. "I want you to lick me clean, from balls to head and back again, until I tell you to stop."
He didn't have to tell me twice! I dove in and wrapped my lips around his balls, taking them into my mouth and gently cradling them with my tongue. I felt a few pubic hairs stick in my teeth as I let go, but I knew I would leave them there all day as a reminder. I ate my own cum on a regular basis, so I needed no encouragement to begin licking my way to the head. I worked slowly and gently, caressing his shaft in an `S' pattern as I slurped down my dripping cum. When I reached the top, I pulled back and kissed the tip. I could see a drop of pre-cum glistening there, so I darted in with my tongue to sneak a taste.
It tasted so much better than my own, so much stronger and so much more pungent. I was ravenous with my hunger for him and began licking my way back down the other side so I could get him back in my mouth again.
"Oh, fuck, you're good." He held my head in place and pushed his cockhead just past my lips, resting it on my tongue. "Just hold it there," he panted, his breath coming quickly, "and savour every ounce of your protein injection."
It only took a few strokes of his cock before I felt him begin to twitch in my mouth. I was so hungry, and so excited, I wanted nothing more than to watch his beautiful cock as the explosion welled inside it. I knew what was expected of a proper sissy, however, so I looked up at his face instead and favoured him with my most grateful, submissive smile of sissy pleasure. I continued to gaze into his face adoringly, broadcasting my satisfaction with my eyes, as his cock exploded.
I don't know if it had been a long time since he'd last cum, or whether he was always so intense, but his cum literally blasted the inside of my mouth. It exploded like a volcano, coating every inch of my mouth with hot, wet, sticky cum. It was so thick, I couldn't easily swallow it, and I was having trouble getting a breath. For a brief moment I actually thought I might suffocate -- a happier death I can't imagine! -- but he took pity on me and slowly withdrew from my mouth.
When he smiled, I finally allowed myself to look away from his face, and gleefully watched the softening slab of man flesh withdraw from my sissy lips. We were still connected by a thin strand of cum, and that image made me cream my panties for a second time that morning. I reached out, freed the string from the tip of his cock, and then lifted my hand so that the cum fell onto my face with a plop. I gently rubbed it in, luxuriating in the feeling of his seed on my skin.
All the while I was gargling with my thick, viscous pool of cum, until there were spermy bubbles popping on my lips. It felt divine, and tasted even better. I poked my tongue out and wiggled it around for a moment, putting on a bit of a show, and then began swallowing. It took a dozen good swallows, but I finally had the bulk of it down, although I would be tasting cum all day long.
Or so I hoped!
"There." He nodded officially as he began tucking himself back into his pants. "Now that I have done my bit to serve and protect, to help a sissy citizen get home healthy and safely, I can get back to work."
"Thank you, sir." I noticed a smear of cum on the back of my hand and licked it off. "I'm sure my recovery will be much quicker, thanks to you."
"You're welcome." He put the mirrored sunglasses back on, but smiled as he did so. "You know, most guys hate this assignment. They complain there's nothing worse than sitting idle, watching a bunch of old farts walk the track, just in case some petty purse snatcher should come along." He looked out the window and stared at the track. "Can I assume you'll be exercising every morning?"
I nodded, certain he could see me out of the corner of his eyes. "And every evening, too, if necessary."
"No, I like mornings." He flicked a switch on the door and released the locks. "You should get going."
"Yes, sir." I opened the door. "Thank you again, sir."
I all but floated over to my bike, prancing and dancing across the broken asphalt, riding a cum-laced high that would last for hours. Unable to resist one last look, I made sure to ride by his open window.
"You know," he called out the window, "you get a much better workout if you keep your ass off the seat. Makes you use your legs more."
"I know, but it gets so hard."
"Sometimes hard is good." He nodded to me through the window. "Get an early start tomorrow, and maybe I'll give you some extra motivation there as well. I find that sissies who can't sit down have a much easier time riding with their legs."
"Yes, sir." I found my legs suddenly shaking at the thought of taking that cock inside my sissy pussy. "I look forward to further instruction."
As I started my ride home, I knew there'd be no going to work today. I saw myself coming down with a sudden cold, the kind that only lots of protein could cure, and the kind that only repeated anal insertions of my biggest latex thermometer could properly monitor. My officer might have been a gentleman today, but I knew there'd be no controlling that monster one he buried it in my ass.
It'd been a long while since I'd been fucked properly, so I figured a day of practice, a day of stretching and straining, was just good preparation for some early morning sissy (s)exercise.
I could really see this becoming a daily routine!
END http://sissygurlconfessions.blogspot.com/