What Every Sissy Knows

Note: the following story is about 99% true with only minor embellishments. For example, there are no condoms in the story. In real life, protection is a must, but stories give us room to fantasize. Enjoy!

*****

I was scared but it didn't matter. I pushed through it until my plump little dick poured out its hot seed onto my tummy. After that all I could hear was the hiss of the shower.

When my senses returned the picture came into focus: I was lying on my back on the floor of the shower, my legs and ass up, receiving in missionary position and my fingers still in my tight ass. I came on my stomach after I failed cum into my mouth. My body yearned for cum, cock...men. But I my head tried to ignore those thoughts. Even now. Even though I had shaven myself smooth, grown my hair out and even came from fingering myself. I didn't even get hard before cumming.

I ignored all that, cleaned myself up as my shame and guilt took over. But even as I stepped out of the shower I saw myself in the mirror: tall, thin, soft skin, wide hips and a shrunken thin cock. I ignored it, dried off, got dressed and hurried off to class as fast as I could.

It was my second year in college, living on my own and slipping further and further towards sissyhood. I was totally closeted and in deep denial. But my urges pushed me slowly closer to what I really wanted.

I had worn the mask of a hetero-male for years and that masculine ego fought me at every step.

I was living with roommates who had no idea as I slowly sissified my self in private. Shaving all over had me nervous; most didn't notice and no one asked. Thank God for Amazon. Box by box, I slowly built up my wardrobe and makeup. It was still all lingerie. I loved everything pink, black and frilly. My hair was growing but I still wore a wig. I was a dark brown brunette sissy with a narrow frame and small but round ass.

Despite my shame, it always passed and I dreamed of dressing up and mincing about. The hardest part of faking was my body language. I could act straight, but all I wanted was to walk in heels and let my feminine instincts take over. I constantly caught myself with limp wrists, swishy hips and a thousand other feminine tells that anyone with a head could catch. When my roommates were gone, I had ample time to dress up and let my sissy side pour out. Swishing and mincing about was often enough to make me bulge in my panties. I smirked to myself when I decided I would need to lock that down soon.

Despite all this, I was still in denial and still closeted. I practiced a lot compartmentalization. I wanted to look up gorgeous naked guys online but still couldn't even cross that line. Instead, I started chatting online. I was a total submissive slut online. Eager to please and serve a dominant man. I genuinely love serving others, being told what to do, worshipping a superior man. It wasn't long before I attracted Richard's attention. He immediately knew what I was and quickly established himself. There was little chat or courting before he declared that he owned me now. It was only online but I eagerly obeyed him.

Richard was a thick-armed wide-chested middle-age man. Short blonde hair, blue eyes and he knew what he wanted (always an attractive quality). He was from across the state border and within driving distance. He wanted to meet up at a hotel near me next week. I was trembling as I accepted his offer.

The week passed by in blur. There were times when I was able to forget what was going to happen to me, but my thoughts eventually turned to Richard. We had everything planned out for his arrival. I was told what to do and I obeyed. He set up the reservation and I went to the hotel room almost immediately after class. When I got to the room alone I exhaled in joy and went to work. I showered, shaved and douched. I brought a few changes of clothes (just in case hehe) but settled on a black and pink-fringed set with a corset, matching garters and stockings and skirt attached to the corset that hid NOTHING. I finished the look with black 4-inch heels and pink-and-black-fringe satin panties. The satin on my little smooth sissy cock and balls was divine. I let it all out and minced, strutted and posed in front of the mirror. I had to calm myself down when I noticed a wet spot on my pantie bulge. I was already worked up and ready for Richard. My male ego may have been screaming but I was too far gone and frankly, horny, to listen. I still had time to back out, but in my head, I was on a one-way ticket to sissyhood. I was reclining on the edge of the bed just clearing my head. A knock at the door nearly frayed my nerves but I calmly got up and swished to the door.

Richard was right on time. We talked out what we would do ahead of time. As soon as he was inside the room we both knew what came next. Without a word, the door closed and I sank to my knees in front of him right there. He was dressed in a light blue button down collared shirt with blue jeans and boots and stood straight up in front of me. They say people show their true selves under pressure. My male ego was completely drowned out by my nervous energy. Instead, I fell completely onto my instincts: feminine, submissive instincts.

On my knees, I ran my hands up his pant-legs towards his crotch. I felt his warm bulge and gently caressed it before quickly moving to undo his fly. My head swirled. This was what I had fantasized about for all my life (and then denied). I peeled down his jeans and then his briefs. His fat thick 6.5 inch cock popped forward. I was stunned and for just a moment, admired his cock. He was cut and 2 inches thick. Its vein pulsed and the shaft throbbed. I was amazed how quickly he got hard. It never worked like that for me with girls. His gorgeous cock and swelling balls were bushy and I loved how masculine he was compared to anything I could have been. I realize I had never seen a real cock, a man's cock. I felt my mouth begin to water and my sissy cock strain in my panties. The f word started creeping into my head: I felt like such a sissy faggot. It only turned me on more.

I paused only a moment, falling in love with his cock, before I touched my tongue and lips to his throbbing red cock head. I licked my wet tongue all around his cock head and them took him in my mouth. I had never been with a man but I had been immersed in years a sissy fantasies. I knew my place. Like a proper sissy, I focused on my man's pleasure first. But I had just enough awareness to savor it: his musky man and cock smell, his salty cock tip. It drove me wild and made me want more. And if it offended my male ego, all the better. I wanted to be as feminine, submissive and gay as possible. My wet mouth and pink painted lips moved up and down the shaft of his cock. I swirled my tongue around his cock shaft, tasting him and loving it. I moved down his shaft, kissing sloppily until I reached his big balls. I gently sucked, kissed and licked just about every inch of his balls.

"That's it Kaylee. Get my cock nice and hard. 'Cause after that, I want you on that bed bent over and ass up."

I looked up at him eyes wide and desperately sucking and loving his cock, "MMMMHMMMMPH!" I gargled on his thick meat.

"You're my little bitch-boy now, right?

"MMMHMMMPH!"

He grabbed my head and pulled me off his cock with an audible "pop". After standing up, I teetered in my heels for a second. I could feel my little sissy cock so hard. If I was in denial before, I reminded myself I was rock hard just from sucking another man's cock. I was hornier and harder for this man than any woman. I was gay. Like the bitch-in-heat I was, I sauntered towards the bed.

Richard smirked and spanked my exposed ass cheeks, "Get your panties off."

I smirked back. Facing away, I bent over and exposed my ass to Richard and his raging cock. He stroked his wet juicy cock as he watched. I peeled down my panties exposing my very pink sissy hole to my man.

"On the bed now, on all fours."

For me, this was it. Once on the bed I assumed the proper position for bitch like me: all fours, on my elbows and arching my back. The small pink skirt of my corset flipped up in this position, presenting my virgin pink ass like the rosebud it was. In between my legs, my smooth sissy cock and balls dangled uselessly. Still, even now my little 4-inch clitty was so hard for my man. Hard and eagerly anticipating his much larger cock. I felt him move behind me and heard him lubing his hard cock.

Thats when I felt it. Just his finger but oh my god I wanted more. I slowly rocked my hips like a wonton whore wishing him to enter me. He gently fingered me but it only made me ache for his cock more. My clitty twitched and leaked for it. Finally, I felt his warm wet lubed head at my hole. I braced myself to be deflowered. I felt warm pressure build at my hole as he began push into me. The pressure built more and more. More than I expected. It was too soon. Then, just as his cock head popped past my hole, It happened, I came! My little clitty was rock hard as he entered me and now poured a thick wet soup sissy seed onto the bed. My body tensed and shot load after watery load.

I tried to hold in my surprise but a few girlish moans and squeaks escaped my lips.

"Holy shit. You just came?" Richard said flatly, knowing full well.

"Uh-huh," I squeaked.

"Wow, what a little faggot."

But the glow of the orgasm past quickly and shame crept back in. I became extra aware of where I was and what was happening to me. Dressed up, makeup, wig and a man (a real man) mounting me, slowly entering me and filling me up. My male ego screamed for mercy and it was all I could do to stay put. Richard sensed my tension and pinned me down to the bed. He was already mostly inside me and thrust the last inch filling me up. Then it started, he began thrusting, assaulting my asshole. On instinct, I bit the pillow.

"HA! Your a real pillow-biter now!"

"MMMMMMPH!" was all I could muster through the pillow.

I felt every thrust. Each one an assault on my manhood. I was paralyzed but didn't want it to stop. I wanted him to shatter what was left of my manhood. It felt good. It felt so right and I let go.

As I submitted to him, to sissyhood, I accepted I wasn't now or ever a real man, but a sissy, a feminine submissive sissy faggot. It was only then I could focus. And really feel him. I felt his thick meaty cock inside me, filling me more than anything before. His thickness pained me at first, stretching my ass. But as I relaxed, pained transitioned into a deep filling pleasure that every sissy knows and loves. I could feel the heat from his cock inside me. My instincts took over and came pouring out after years of suppression. As he continued to pound my fag pussy, I felt his cocktip hitting a sensitive nerve. He hit my prostate! Every pound building toward another orgasm.

I gave into long repressed instincts, working my ass, meeting his thrusts and most of all think about his pleasure. Knowing I was now a subby little bitch all I wanted to do was please him. Any shame left was completely overwhelmed by the sensation of being dominated by a man. I didn't feel like was playing sissy anymore, now I was a sissy.

I was just starting to savor each thrust of his cock sliding in and out of my fag pussy when he pulled out completely. He turned me over and spread my legs. I'm sure I had a scared look on my face but he just smirked. I loved it. My instincts served me well as I rested my legs on his shoulders. I positioned himself right at my door and eagerly anticipated his reentry.

"Beg for it sissy"

"Yes please daddy please! Please fuck me! Please fuck my faggy ass!" I'm usually more eloquent but it felt so good to say.

He looked me right in the eye as he entered me again. I relaxed and cooed as he filled me. He started to fuck and pound my tender hole nice and deep. I felt his balls slapping my ass. God I loved it. He leaned towards and I met him so eagerly.

There are some sissies who have little interest in men. But there's no hope for sissy fags like me. Even while filled with Richard's hard member, it was electric to hold this man close, kiss him and feel our tongues intertwine. That was how I really accepted my love of men: not just fucked and dominated but lovingly serving, kissing and caressing him.

It was too much and I knew I was going to cum again. I squealed and Richard felt me tensing.

"You're gonna cum sissy?"

"Yes! Yes! Fuck me daddy! Fuck my faggot ass!"

He shot up straight and started pounding my submissive ass hard! My little half hard clitty started bouncing back and forth. It felt so good I cupped my padded breasts and spread my legs further on instinct. I moaned and squeal like a true sissy as another orgasm made me convulse and shoot another watery impotent load.

I knew I did a good job because that was too much for Richard: he grabbed my hips and plunged every inch of himself into my hole. My mouth gaped from sheer impact of this man's hard cock inside me. It was exquisite feeling Richard tense and throb ashis cock pump load after load into my wanting asspussy. I worked and gyrated my hips milking his manly cock with my pussy.

I held him close in that position. Kissing him and tasting him. I think my tenderness surprised him but it also enticed him. I was absolutely dripping with semen both mine and Richard's, on my tummy, my clitty and my boi pussy. I savored the moment without an ounce of shame. I knew my place.

Afterwards, we continued to make out and he joked about how easily I came. I would have been self conscious about those things as a man but I knew that was over. And my faults and weaknesses as a man we're now my strengths as a sissy. He kissed me and spanked my ass before he left with his things..and my manhood.