Sissy Crissi Ch. 03

Chapter 3 -- Leroy's Turn

But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers into my crack, grasped my cheeks firmly and squeezed hard.

"Oh yeah, that's one fine ass you got there, slut!"

I knew I shouldn't feel the way I did, but I couldn't help it, somehow he made me feel proud with his compliment. I did have a great ass - round and smooth and firm. When I got all dolled up and looked at myself in the mirror, I wanted to fuck me. But kneeling there, dressed like a total whore, with an absolute beast of a man poised to rape my virgin ass, I was feeling that maybe this had all gone too far. It was true that I had sucked my first cock, and it was also true that the experience had ended with me cumming in my panties, but I hadn't bargained for this. I didn't want any part of being speared by Leroy's giant pole, and besides, there was the real world. In the real world I was male, maybe not very manly but definitely male. I had my job to worry about, my friends, my whole life.

My mind raced between the thrill of the moment and the reality of what would come tomorrow. I was filled with lust but fearful of the pain. I knew I should try and put an end to this scene right there and then. But as Leroy continued to massage my finest asset, sliding his hands over my silky cheeks, tracing his fingers gently along my satin crack, all I could think of was how good it felt. His strong hands on my body made me shudder. My pulse quickened with each ensuing touch, and despite my exhausted state, despite my reservations, my breathing gradually grew faster and before long, I began to pant with excitement.

Kneeling down behind me, Leroy pressed his growing bulge against my ass as he reached forward, held me with his hands clasping my hips, and pulled me tightly against him. Even at this stage, the feel of the monster in his pants made me both shake with excitement and shudder with fear. One part of me wanted to just get up and run, but the other wanted nothing more than for Leroy to fully make me his bitch. Without thought, I responded. I pressed my ass back against Leroy, moaned out loud, and returned my face to Erika's exposed love hole.

With that, Leroy had all the encouragement he needed. "You Daddy Leroy's now, bitch." Leroy's tone was soft, yet matter of fact. There was no hiding it, my actions had left no doubt about my desires.

With my face buried in Mistress Erika's pussy, Leroy held me tightly and jerked my ass back toward him, pulling my head from between Erika's silken legs. Leroy loosened his grip, stroked the front of my thighs, down my stockings, nearly to my knees, and then with a relaxed hold around the front of my skirt, bent forward and whispered into my ear, "You are one hot little cunt."

Oh my god! His words sent a bolt of lightning straight between my legs. The confidence and control in his manly voice made me swoon. Leroy was all man, all stud. Large and muscular, his rock hard physique was a thing of masculine beauty. He reached his powerful arms around my chest and fondled my silicone breasts. Rubbing them as if they were real, he made me feel feminine like never before. He slowly moved his hands from my breasts and then holding me firmly around the waist with one arm, pulled my hair from the side of my face and gently kissed me on my neck. It was all so soft and gentle. I could feel his hot breath as he brushed my cheek with his lips.

"You like being my bitch, don't you sweetness?" Slightly above a whisper now, his voice was still soft and enticing.

"Oh yeah, you like my big nigga hands rubbin' your hot little white ass."

"You a nasty little slut, ain't you bitch?" Holding the cheeks of my ass, again firmly cupped in his strong hands, he lifted me upward, straightening my knees.

"Nuthin' Leroy likes better than a nasty little whore." He reached from behind and stroked my half-hard clitty, still pressed between my legs.

"You my nasty little whore?" His fingers slid slowly away from my clit and found my bud. He pressed his thick digit hard into my virgin hole, "You my whore, crissi...you my cock whore?"

"Crissi?" Leroy had used my name and somehow that changed my thoughts. It was so personal. He had me purring as he tantalized me with a caress far softer than anything I had expected from Leroy, and now he referred to me by my name... Any resolve I had had to stop the scene, to salvage my male identity, was slowly being stripped away. Leroy was seducing me, and with each gentle stroke, with each nasty whisper, I wanted more and more to be his.

"Oh yes...yes Master Leroy -- I am your bitch. I am your whore," I cooed, now looking back over my shoulder, resting my arms atop Erika's thighs. The site of Leroy's Adonis figure kneeling behind my uplifted skirt and exposed stocking tops was more than I could take. I became completely lost in the moment.

How blissful it all was, my Master treating me like a woman, a fine sexy woman. I was enjoying every minute of it. I began to feel confident in myself, for the first time. I was an object of passion. I was no longer the little guy with the puny dick. I was a hot seductive bitch, from my stocking feet and red heels, to the long flowing locks of my hair. I was the one who was making Leroy act this way. It was my sensuous form, my round curves, my fine firm ass. I felt female -- hot and sultry, and I wanted to please my man.

"Fuck me Master Leroy, fuck your bitch," I purred, my voice low and inviting.

Without another word, Leroy reached up under my skirt and grabbed both cheeks of my ass in his hands and squeezed, hard, taking my breath away, making my tight virgin hole pucker.

"Yeah baby, I'll take this ass"

"Oh yeah!"

Leroy let go of the bare skin of my ass and began to rub my upper thigh. The gentleness was all but gone now. Running his hand over my garter and stocking top, he reached around in front of me to again feel the growing hardness between my legs. He confirmed what he already knew - he was having the desired affect on me. He circled his rugged hand around my thigh, across the smooth cheek of my ass and started pressing his finger once again through the satin of my panties, hard against my anal bud.

"You ready for some cock now, bitch?" His tone had turned forceful. He wasn't asking. He was giving me a warning. Leroy continued to probe my crotch, massaging me through my panties for a moment, but then grabbed my hips and pulled me back hard against his massive bulge. He forced his hips forward and ground his cock against my exposed ass.

It was the monstrous size of what I felt press against my ass that snapped me out of my lustful haze. I couldn't do this. I knew the pain would be unbearable. What had been so arousing, so sensual, had changed in an instant. I felt fearful of what was to come. I looked up into Erika's eyes but they were still closed. I pulled free from between her thighs, turned as far as I could within Leroy's grasp, and began to plead.

"Please Master Leroy; I can't take your cock. It's just too big, please... please sir."

Sure, I had played with anal stimulation many times, and I did so enjoy it. I wish I didn't, but I did. It always made me feel like such a slut. But no matter how many times I had played, I had never had anything up my ass that even compared with Leroy's giant cock. I began to shake as I thought of him spearing my tiny hole with his massive rod. He would split me in two.

"Please Master Leroy," I cried.

"Please just let me suck you. I'll," he cut me off.

"Shut the fuck up, bitch."

"I've had your mouth. Now I'm gonna fuck that tight little ass-pussy of yours!"

With my hands resting on Mistress' knees, I watched as Leroy dropped his trousers and pulled his monster cock from his shorts. The massive snake instantly came to life as he shook it out. He knelt behind me, cock in one hand, the other firmly holding my upper thigh.

"Oh, you're gonna fucking take it, slut."

"I'm gonna fuck you like the cunt you are."

"You're gonna love my nice big cock in that tight little sissy ass of yours."

"Mistress!" I pleaded in desperation, hoping for some sort of reprieve. Arousal had become completed replaced by fear.

"Mistress, please..."

Erika finally opened her eyes, reached to me and softly held my arm. "Oh, that was so good, baby." It was clear that she had been in her own world.

"You really are a fine little pussy licker."

"But it's Leroy's turn now, sweetie."

"Oh no, Mistress. I can't," I pleaded again, maintaining respect and being careful not to look her in her eyes.

"Now crissi, you know you're a little sissy gurl, and all little sissies must serve their superiors. Leroy has been very patient." Erika spoke in a calm tone as she gently took my hands in hers and squeezed my chest between her legs. Then leaning forward, she held my chin, raising my face to meet her gaze.

"You are our sissy now, sweetie. You belong to Master Leroy and me."

"Your duty is to serve and pleasure us as we see fit."

"You do understand, don't you?"

"Yes Mistress," I replied, knowing I was beaten. I slumped into her lap.

"And we both know how much you love Leroy's big black cock..."

"Now apologize to your master and ask him if he would please allow you to service his wonderful cock. Offer your little sissy-pussy to him, sweetie. Tell him how much you want him to fuck you with his big hard cock." I was like putty in her hands. I couldn't say "no" to her.

Leroy had backed off slightly during our exchange. He was now standing behind me, still holding his cock in his hand. I pulled my skirt down to cover my pantied ass and garter straps, and pivoted around on my knees to face my black master.

"Sissy is sorry Master. Will you please fuck your sissy?" I couldn't believe the words had come out of my mouth, but I didn't know what else to do. I wanted to please Mistress Erika, and I did so love Master Leroy's gorgeous cock, but the thought of the pain that was to come had completely drained my desire. It was like I was under her spell, in some hypnotic state. I was just going through the motions.

Leroy stood with a smile on his face, both hands on his hips, all man, looking down at my groveling sissy form. Crouched at his feet, sitting back with my panty covered ass resting on my strappy red heels, I placed my long painted nails on my thighs, covering most of what was peeking out from my skirt, and I waited for my Master's response.

"Now we're gittin' there, but you gonna do better."

"Tell me what you want, bitch," Leroy commanded.

"I want your cock Sir," I said, first without feeling, but then hearing the words come from my lips, felt a sudden twinge of arousal start in my loin.

"Make me believe it, cunt!" Leroy seemed to be loosing patience.

"Please Sir, will you please fuck my sissy ass with your hard manly cock." Oh, that was it. I was still torn, but as the words escaped from my mouth I knew they were real. Just hearing my voice utter the words was an admission. I was a sissy, a wannabe cumslut. I was begging another man to fuck me in the ass, and my little sissy clit was getting harder by the moment. If I had had any dignity left, it was gone now.

There I sat in complete submission, the scent of my distinctly feminine perfume filling my senses, my sissy-tits hanging heavy in my lacy bra, my head hung low. I respectfully stared at Master Leroy's feet, my long curled hair falling over my shoulders, partially covering my soft red cheeks, and I anxiously awaited my master's response.

"That's a gurl. Now come get your master hard."

I eagerly complied and did as I was told. I sat up on my silken knees before Leroy. I wrapped my small feminine hands around his massive shaft and first licked it like a lollipop. It immediately jerked into action, hardening more in an instant. I pressed his huge helmet head to my mouth and parted my lips to force the monster inside against my tongue. I swirled the base of my tongue against his swollen man flesh, then pushed his cock from my mouth, kissing the head as it exited. Again I hungrily licked the length of his heavily veined shaft, then around the underside of his huge mushroom head, and returned to tease his piss slit with the hardened tip of my tongue. Slowly I squeezed his shaft, just behind his cockhead, forcing a generous flow of precum onto my waiting tongue. I greedily sucked it into my mouth and pressed it against my palette. I savored the taste for an instant then again passed the swollen head between my lips and sucked it to the back of my throat. He was now completely hard as he grabbed my head and started to slowly pump my mouth.

"That's it bitch, get me good and hard, you sissy cocksucker. Oh ya."

My little sissy clit was now straining against it silken confines. Erika was right. I did love his hard black cock. Though I wasn't a sissy cocksucker - I was a sissy cock-worshipper. I loved everything about cock, the smell, the taste, the soft flesh and the manly hardness, the large head, the rigid shaft, and oh my, the hot sticky cum. The only thing I love more than holding a hard cock in my hands is slavishly licking and sucking one until it explodes in my hungry mouth. As Leroy fucked my face I knew that they were both right, I wanted to give Leroy my anal cherry. I wanted him to pound my sissy ass and make me scream. I wanted him to fill me with his studly seed and make me his bitch. It was then that I knew that I could no longer call myself a man. That identity was gone, a part of the past. I was now a bitch in heat and I wanted nothing but to be a wanton sissy cumslut.

"You ready for my cock, bitch?"

"You ready to ride my hard black cock?"

Leroy pushed my head from his crotch, forcing his cock from my mouth.

"Yes Master, oh yes," I squealed, as I licked and savored his musky taste on my lips.

"Please take me. Please make me yours" Fuck! I was so embarrassed to act like such a fucking sissy fag in front of Erika, the woman of my dreams, but I had no choice. I wasn't following orders anymore. I was burning with desire. I was a cum-crazed sissy bitch and I wanted that massive cock buried in my virgin ass.

I quickly spun around, turning my ass toward Master Leroy and fumbled to pull my panties down. I tugged them to my knees, and then I lifted my skirt up on top of my back, completely exposing my firm round ass. I looked back at the garters framing my smooth shaven cheeks, down my stocking covered legs to my strappy red Hussies. I looked beyond, to Leroy, still standing, stroking his enormous cock. The scene was almost more than I could take.

With my eyes fixed on Leroy's glistening cockhead, I struggled to tug my panties from around my knees. I quickly pulled them down my calves and over my heels, and then I spread my legs as far as I could. My little cockette immediately sprang free from between my thighs and stood at rigid attention, saluting the masterpiece cock that was about to take my anal virginity. I reached back, placed my long painted finger nails on either side of my opening and spread my cheeks as wide as I could. Looking back at Leroy, I cried, "please Master, please fuck your sissy. Please fill me with your hard cock. Make me your bitch."

Holding my ass spread wide, I turned to Mistress Erika, her skirt still hiked around her hips. She was slowly fingering herself, obviously aroused by the scene in front of her. She lifted her legs once again and placed them over my shoulders, "Eat my pussy," she murmured.

I let go of my ass and caressed Erika's thighs. Leaning forward with my sissy breasts resting on her silky legs, I slid forward and found her moist crevice with my tongue. The pungent scent of her female privates, so recently exploded in orgasm, filled my senses. I began to lick and probe her pussy with loving adoration.

Leroy now had both hands on my exposed ass. He dropped to his knees and I felt the cool sensation of whatever cream he used to lube my tight little virgin ass. Leroy smeared the grease on my ass, pushed his finger against my hole, wiggled it back and forth a couple times and then rammed it into my waiting hole. I couldn't help but moan.

"You like that, don't you slut?" Leroy said as he probed my prostrate.

"Oh yes - yes Master," I cooed, momentarily pulling my head from Erika's love hole.

Without stopping, Leroy continued to massage my anal cavity with his thick finger, feeling around, side to side, as he pumped it into my opening. He stopped and pushed hard and deep, as if trying to see how far he could penetrate. I returned pressure, forcing my hips back against his finger, and moaned with pleasure, "ahhh, oh yes."

"Shit! You are one fucking horny little slut," Leroy chortled as his probe jerked in my ass.

"You ready to be filled with hard black cock?"

"Yes Sir, please fuck me, please..."

"Beg me, bitch, beg for it. Beg to have your candy ass filled with cock."

I responded without hesitation, "Please fuck me, Master. Please fuck your sissy with your wonderful black cock."

"Please fill my pussy with your cum."

"Please make me your slut!"

With that Leroy grabbed my ass, spread my cheeks and pressed his hard prick against my slippery hole. Pushing the huge head of his monster cock against my tight opening, he grabbed my hips and forced his entry into my most private place. The pain seared through me like I had been split in two. I involuntarily started to pull away from the pain, but Leroy's grip tightened and held me in place. Leroy then yanked me back to him, forcing his cockhead through, opening my ass wide. Another stabbing bolt of pain shot through me, and I began to regret again that I had ever gotten myself into this horrid situation.

Another strong push and the head of the hard cock in my ass was fully inside. The pain briefly lessened, but then Leroy pushed again, forcing a good 4 or 5 inches of his thick steely hardness into my burning ass canal. I gasped loudly at the pain, then let out a shrieking scream as he began to push deeper. Tears filled my eyes. "Please stop Master Leroy, please stop, please..." Tears streamed down my face as I sobbed.

Mistress grabbed my head and pulled me back to her still wet pussy, "I told you to eat me, bitch," she commanded as she held my head forced between her thighs. My sobbing, my screams, were all now muffled by the pussy she smashed against my face.

I tried to focus on her juicy snatch, sticking my tongue in as deep as I could, but another push from Leroy, and he nearly ripped me apart, fully burying all 10 inches of his hard black manhood deep inside me. I could focus on nothing but the huge cock invading my burning ass. My entire body spasmed with pain and my little cockette fell limp between my legs. I began to whimper, my body shaking as I cried.

"Shut the fuck up, cunt!" Leroy said in a commanding tone, as he began to pump his cock in and out. "This is what you wanted, and you're going to love it."

But the pain was more than I could take. I pulled back from between Erika's thighs one more time and pleaded with Master Leroy, "Please no, Master...ahh, no," but the pounding continued.

"I can't take it," I screamed. "It hurts so bad, please..." I begged.

"Fuck you, cunt," Leroy yelled as he slammed his cock deep inside me. "Sissy cunts need a good, painful, ass fucking."

"Dress like a whore, get fucked like a whore." Leroy held my hips as he started his piston pounding of my sissy ass.