Moon-Eyed Sissy

"Open up, girl..." He said impatiently, pressing his massive head firmer against the seam of my lips.

At this point I had a choice to make - do nothing and be forcefully made to suck another man's cock, or find and embrace the sissy within and do it willingly. Where is she? I wondered. This wasn't like the training videos at all. This warm, throbbing boner pressed against my cheek was not the same as the cucumbers I had practiced on. Still, I wanted the latter option. I needed to try and reawaken my sissy desires, somehow convert or carry them over from the hypothetical realm to the actual.

I parted my lips just a tad and the very tip of his penis slipped in and rested against my teeth. The head felt strange and horrible on my lips, the skin hot and textured, and I wanted to cry. Instead, I opened my mouth wider, and slowly my father-in-law pushed half the length of his soft member into my mouth. It was throbbing as it sat my tongue, and I could feel it stiffening inside of me. I gagged, even though it hadn't touched my throat, I and thought I might throw up. So gross.

In the mirror, I caught a glimpse of myself, on my knees, mouth full, eyes tearing. I should have listened to Mom, I thought morbidly, as if this was something she had warned me about. Katie's dad sensed my cooperation and loosened his grip on my hair as I started to work, running my tongue up and down the length of his shaft, the taste of sweat lingering on my taste-buds. By the time he was fully erect, his cock was a monster. I couldn't take more than half of it into my mouth, and though I had trained myself to suppress my gag reflex, I still dry-heaved every time it tapped the back of my throat. He kept forcing it in deeper than I could take and I was hating every second of it.

Where are you, sissy?

I looked up at the man, meeting his gaze as I teased around the ridges of his head with my tongue, and I batted my mascaraed eyes at him. It seemed like the sort of thing a sissy would do, but it felt awkward and not fluid at all. He didn't look unhappy, exactly, but he did look kind of bored, unimpressed. He hadn't given me any positive feedback at all, not even a moan of pleasure. I don't know, I just couldn't get a rhythm going, the cadence of my stroking and licking totally uneven. I was too nervous, unsure of myself.

"Thought a sissy would be better at this..." He said, disappointment in his voice, and my heart dropped. He'd all but let go of my hair.

"I've...never done it..." I replied sheepishly. "Sorry..."

"Don't go apologizing." He said, and I think he was actually cringing for me, maybe some pity breaking through his mean exterior. "Ain't you ever watched porn? Seen how a real woman works one o' these?"

"I do watch porn." I pouted, and then felt dumb for defending myself on that point. He pushed me off of him, then, and my tongue slid down and off of his manhood wetly. I felt like a failure then, and my disgust at the situation blended strangely with that feeling.

"I got an idea." He said, and he turned and walked into the bedroom. I followed him, numb and passive, and he continued on into the living room. He relaxed onto the futon and put his arm over the back, beckoning me to sit. Reluctantly, I did, and his arm enclosed me, his hand resting on my shoulder. "Turn it on."

"What?" I asked, confused.

"The porn. Turn some on the TV there." He said, gesturing toward our living room television. "Show me what you like."

"Okay..." I said quietly and pulled up my phone. I searched my recent videos for something that wasn't a sissy training, and when I'd found something decent, I cast it onto the screen. We waited in silence as it loaded, and my heart was pounding. We sat through an obnoxious ad, and then the video began. I remembered this one, sort of. It was a casting-couch style scenario, and by coincidence, the actor's positions mirrored our own, seated side-by-side on a couch.

"Now that's a woman." My father-in-law said, eyes locked onto the screen, staring at the heavy-breasted actress, her curved figure cradled beneath the arm of the "casting director" just as I was cradled beneath my father-in-law. Could he grab me if I tried to run now?

"That's you, sissy. So pay attention. Follow along." He commanded, and I understood, my brain searching for some extended memory, some remembrance of which sex acts would be performed in the video. Little came back to me, though I doubted anything particularly avant-garde would occur.

First, the woman unbuckled the man's belt, helped him remove his pants. I glanced at Katie's dad, and he looked at me expectantly, one eyebrow raised. I let out a sigh and started to undo his buckle for him, undid the button of his jeans. His zipper was already down, his cock - mostly flaccid again - unsecured in the open air. He lifted up slightly and helped me to pull his pants away from his waist. Then I removed his boxers, using one hand to guide his shaft through the hole in the fabric.

Second, the woman massaged the man's balls while preparing his shaft, stiffening him with one hand. My father-in-law's testicles were sized in proportion to his cock, his sac heavy and warm. I carefully cupped his balls and gave them gentle squeezes, his skin loose enough to slide between my fingers, and I found that I didn't mind the sensation. My other hand was lightly massaging his shaft and I had to focus to keep both motions fluid. As I copied the porn-star's methods, the cock began to stiffen with an eagerness that had been missing before.

"That feels amazing..." He said, leaning back. Now we're getting somewhere, I thought, and something sparked inside of me, finally. My face was a blush.

Third, the blowjob. I had already failed to perform effective oral on this man, and I was nervous to try again. I watched the woman on the TV closely, mirroring her movements. She spit on the head of the cock, and I did the same. In my anxious state I wasn't precise and most of the spit just dribbled onto my chin. I wiped it off with two fingers and used my hand to wet him with it instead. Out of my peripheral, I watched as the woman gulped down her co-star's lengthy rod, how she pursed her lips around it, pressed her tongue against it to increase grip and lubricate, how she continued massaging the balls all the while.

I didn't have her skills or dexterity, and I lost my rhythm sometimes, but with the video in the background as reference, I was able to find a comfortable cadence. Up and down, over and over, I took Katie's father inside of my mouth, breathing through my nose, tightening my lips, doing everything I could to make my lips feel like a pussy, if not better. My inner sissy was awakening, and my cock-lust was waxing, my nausea waning. My mouth was watering at the taste of him, at the texture of the veins winding along the length of his meat. There was lip gloss on his shaft.

"Oh, fuck..." He moaned, and I echoed it back, but feminine. My father-in-law's cock was throbbing, pumping then, feeling alive in my mouth, and I was sure that he would blow his load. I prepared myself, mentally, but he was saved by the bell. The porn changed and we mirrored it perfectly in the next moment as he grabbed my hair and forcefully pulled my bobbing head off of his shaft. A tiny spurt of pre-cum wet my lips as the head of his cock slipped out, and I felt a surge of mixed revulsion and curiosity. I just let the watery fluid drip off my lips and down my chin, too shocked to lick or wipe it off.

The woman in the video switched positions, sitting up on her knees, still on the couch, leaning over and into the man's lap, ass raised into the air. I did the same, my skimpy pleated skirt barely covering me. Katie's dad played his role, too. His left arm, which had been draped around my shoulders, slid across my back and then gripped a handful of my ass-cheek. He squeezed hard and a little whimper escaped from my mouth.

I teased the tip of his shaft with my tongue. The woman in the video was blowing her co-star again in full force, but I used my discretion here to deviate from the script, worried that my father-in-law would finish immediately if I started up again so soon. He didn't seem to mind, perhaps too focused on his own part to notice. His hand caressed my raised ass eagerly, exploring the shape of me, spanking me like he probably used to spank Katie. After my cheeks were red from his repeated slaps, his fingers began to press against the taut space in my panties, searching for, and then finding, my asshole.

Through the fabric, he used one finger to apply pressure, and waves of pleasure radiated out from my sissy pussy. My legs were shaking, and he had unlocked me. I was in full slut-mode then, and all I could think about was whether I was about to lose my virginity. Does his finger count? I wondered. It hadn't actually been inside me yet.

With my tongue slapping wetly around the ridges of his head, I reached down between my legs and ran my palm along my own shaft. I'd been stiff for a while, almost numbly so, my panties hugging and pressing my protruding shaft against my pubic region. I was tiny compared to Katie's dad, even at full mast the tip of my seemingly substandard cock didn't reach my belly button. I used my open palm to rub myself as my father-in-law continued to tease my asshole.

I was on the edge within moments, and he pushed me over it. He pulled my panties aside rough-like, probably stretching them, exposing my asshole. I arched my back for him in response, guessing what he wanted. He was done teasing, instead pushing two fingers inside of me and massaging. It all happened faster than I was expecting with no chance to relax, so it hurt badly, but it also nudged me into orgasm. A rope of ejaculate shot from the tip of my cock, white semen flooding the inside of my pleated skirt, white on peach.

The semen kept spilling out of me, more than I thought possible, my orgasm sustained by the fingers still fiddling with my alt pussy. The front of my skirt was soaked through and my entire body was trembling, gone weak. I collapsed forward, laughing, literally unable to support my own weight after what Katie's dad had just done to me. My face slid down and planted itself squarely on his balls, and I think I was drooling, my tongue hanging loosely against the skin of his testicles.

"Oh my god..." I muttered, feeling as if I'd floated to heaven and then fallen back down again.

"You loved that, sissy." He observed, declared, his fingers still inside of me. I turned to meet his gaze and nodded shyly, my heart fluttering and my body still humming.

He let me rest for a minute, still fingering me, but with less intent. I licked his balls idly, his shaft lying back against his stomach unattended, but still quite hard. My eyes were drawn to the television. The woman there continued to perform oral, but I knew we must be close to a scene change. Sure enough, in the next few seconds, the pair began to reposition, and as they did, my father-in-law pulled his fingers out of me. I looked up at him, questioning, a pouting lip. He nodded to the screen.

Fourth, the cowgirl.

"I wanna ride you, daddy!" The woman on the screen proclaimed, energetic, and she mounted her partner, sliding his shaft inside of her pussy. It was really stretching her out, I noticed, but she didn't protest. She was a professional. She started to bounce on it and my father-in-law gave me a hard spank.

"You ready?" He asked, eyes locked on the screen, entranced. I said nothing. Time to return to the script. Katie's soiled skirt felt uncomfortable then, the semen I had spilled on it no longer warm, the fabric sticking to my thighs. I stood up on the futon and let it drop to my feet, kicking it away. Then I removed my blouse for good measure, tossing it out of sight. My lacy pink panties I kept on, and my flats. My groin was at his eye-level then and he was staring at my little bulge with lust in his eyes.

"Do you like it?" I asked, turning so he could see my package, or lack thereof, from different angles. He said nothing in reply, at least, not with his voice. Fuck the script, I decided, feeling more confident. Still standing on the futon, I stepped across the cushions so that my feet were on either side of my father-in-law and my girlhood was centered on his face. Then I returned the favor from earlier, leaning forward and pressing myself against him, grinding my little girl cock on his face, the thin fabric of my panties still covering and containing me.

He didn't protest, and I felt the air move as he sucked in through his nostrils, savoring my scent. He would mostly smell perfume. He gripped my ass with both hands, pulling me in tighter, and I felt his tongue exploring me above my women's underwear, looking for a way beneath them, wetting the fabric with his saliva. His attention was stiffening me again already. With both hands, Katie's dad slid my panties down. They got stuck around my knees, but it didn't matter.

My father-in-law took me inside of his mouth, then. All of me, my testicles and cock both. I was small enough that he could do it, and I squirmed as his tongue explored. It hurt a little, my cock feeling sore from having just cum, but I didn't want him to stop. He started sucking on me like a pacifier, and despite myself, almost without any buildup, I rode a lesser wave of pleasure as small squirts of cum pumped out of my tip and directly into my father-in-law's mouth. He kept suckling until it was uncomfortable and I had to pull myself free, insistent. I was completely soft then, my sissy regions dripping with saliva and semen just outside of his lips.

I started to pull my panties back up, but he grabbed them and yanked, buckling my knees. I collapsed on top of him, straddling him.

"We're ain't done, girl." He said sternly. Of course not, I thought, but my two orgasms in such close proximity had taken much of the steam from me. I had almost forgotten that he hadn't finished yet. Behind me, on the TV, there was an almost constant, theatrical moaning, the woman still riding on top. I glanced back and caught an eyeful as the man finally burst, his ejaculate sneaking in sticky white streams past woman's pussy lips and down his shaft.

"Do you want me to ride you...Daddy?" I asked, trying on the word. His cock twitched when I spoke it and a sleazy smile appeared. Does Katie ever call him "Daddy"? I wondered. My soft sissy things were resting on top of his massive genitals, and the difference in size was preposterous. As I compared, it occurred to me that I've never really been a man. "You're really big."

"It ain't gonna fit." He admitted, surprising me, his hands gripping my waist. I knew it wouldn't, but I didn't think he'd care, thought he would ruin my hole forever to get himself off. "Could barely get two fingers in there."

"Maybe...just the tip?" I offered, though the head of his cock didn't taper much. I was willing to try, wanted to, even. I started warming him up by rubbing his shaft with the palm of my hand.

"Ain't gonna fit." He repeated, matter-of-fact. I leaned forward on my knees and lifted my ass up, used my hand to stand his cock up and rest it between my cheeks behind me. As I leaned over him, he licked one of my bare nipples and I was surprised at how sensitive it felt, how pleasurable it was.

"Tease me, then..." I whispered into his ear, "...Daddy."

And Daddy did, gripping the base of his shaft beneath me with his right hand and guiding it toward my sissy hole. He zeroed in and started tapping the head against my star. I giggled, and my face was close to him, so I started to kiss his neck. He grabbed my hair firmly and yanked my head up, then pressed his lips into mine, and we kissed for the first time. He tasted like my own semen.

I slipped my tongue into his mouth, and relaxed my asshole, letting his head press in just a little. For a moment, I was outside of myself, and as I made love to my bastard father-in-law, I thought of Mother and Father and my wife, Katie, who I thought was the love of my life. My life, in which there was then a clean divide, a before and after. This evening had changed me, solidified my form. I would be a sissy forever, for better or for worse. There was no return path.

Just one more thing to do.

Relax, sissy.

I let out a deep breath and used my weight to carefully force the head of his penis inside of me. Waves of pain radiated out as it penetrated me, but I didn't tense up. I used his shoulders to stabilize myself, commanding my body to accept his manhood, his blessing from God, my sissy coronation. When Daddy realized I was going for it, he cupped my cheeks and pulled them apart, spreading me. Slowly, push after push, we worked together to shove an entire quarter of his shaft inside of me.

"You're so fuckin' tight..." He breathed, and then "Can't go no deeper."

He was right, and I nodded in agreement, my face a mask of endurement. I felt as if I'd be stretched forever from what we'd already done. On every breath, my muscles tensed, squeezing him, and I hoped it felt good for him. There was no pleasure in it for me, at least not physically, and I couldn't bounce on it like the woman on the casting couch. But I felt pride, still, felt accomplished. For a few moments we just existed, our bodies one entity. A thought occurred to me.

"You just deflowered me..." I said, and genuine surprise flashed across Daddy's face.

"Wait, you're a virgin?" He asked, incredulous, and I felt his cock throb inside of me.

"I was one." I corrected him.

"You and Katie never...?"

I shook my head.

"The bitch is a prude, just like her Mother." He said, grimacing, and I didn't disagree with him. Somehow, speaking plainly, honestly with my father-in-law was the most vulnerable I'd felt all evening. I'd never spoken with anyone about my marriage problems, especially not that one.

"I hate her." I admitted. Daddy's expression softened, and if I had to guess, I'd say he saw something in common between us then. He pressed a kiss against my lips, surprising me. It was passionate, somehow more erotic than the hardcore sex we had been engaging in. His cock was still throbbing inside of me, a supremely uncomfortable feeling which clashed against my sudden emotional high.

"I have..." I whispered between kisses. "...an idea."

I reached down below me and began to jerk the base of his shaft, the length which was not stuck inside my asshole. He was into it, and every-so-slightly began to pump with his hips. The undulations caused me sharp pain on each thrust, and he only had about a centimeter of give, but I braved it. Based on how wild his eyes had gone, and how I could feel his heart pounding, I didn't expect him to last long. My expectations were in line with reality. As he neared completion, he shooed my hand away and took over, stroking the base of his own shaft powerfully, knowing exactly how to get himself off.

What escaped his lips was more of a yell than a moan as my father-in-law, and more importantly, my Daddy, unleashed his sperm inside of me. A girl never forgets her first time, and I'll never forget the feeling of warmth, the feeling of fulfillment, that washed over me as liter of white, hot ejaculate flooded my insides. It took ages - horrible, heavenly ages - for his member to stop throbbing, to stop ejecting seed into my asshole. Nothing leaked out of me, not like the woman in the porno. There was no room, my pussy plugged tight.

"Fuck yeah." He sighed, leaning his head back and closing his eyes, his hands dropping.

"I might get pregnant." I whispered for some reason. It was an absurdity, but it felt sexy to say. Daddy chuckled, one of his hands idly massaging my left nipple. After a minute or two, his manhood softened a bit, and the tension lessened in my permanently-expanded sissy hole. I felt warm, viscous liquid streaming out of me, and we both looked down to watch it flow down his shaft. Beautiful. Another few moments, and he was flaccid, and Daddy pulled his shaft out of me without much drama. I was uncorked and creamy ejaculate poured down my legs.