tagTranssexuals & CrossdressersA Debt Left Unpaid Ch. 02

A Debt Left Unpaid Ch. 02


The first thought that crossed my mind when I saw Vito was that I'd be dead within the hour. My second thought was wondering how large a man of that stature's cock would be. I figured I would have an opportunity to find that one out for myself, like it or not. I was sitting opposite him, a solitary candle sitting between us, flickering shadows across his otherwise handsome face. He crossed his tanned arms and waited for me to take my first sip of the wine that he'd chosen for me.

"It's a '63 port that I'm sure you'll find delectable." He assured.

I lifted the glass to my lips and gulped the contents, I smiled shyly and returned the lipstick stained glass to the table, deftly dabbing my mouth with a lacy kerchif.

Vito eyed me as I gulped the wine, "My kind of woman!" he chuckled, scratching his scruffy jaw.

Thomas, who was standing nearby with a pristine white towel draped over his arm, immediately filled my glass back to its brim.

"So as you might know by now...our meeting here is sort of a strange circumstance." He began, his sweet smelling cologne reaching out to me with odiferous fingers.

Nodding, I gulped another mouthful of wine.

"Now I'm not going to make you do anything you don't want to do..." his eyes lingered in my cleavage, and I could feel them, and oddly, they excited me.

I wondered if this was how all girls felt. I traced the rim of my glass coyly with my index finger, my head already a bit dizzy from the wine.

"You see, your friend Sarah owes me quite a bit of money indeed, and while I am what you might consider to be a man of...well lets say exuberant wealth, but I do not appreciate liars, deadbeats, and people of that nature. So I had to send my associate Saul to have a conversation with Sarah, and she offered you and whatever services you offer to me in return for a valued commodity, ...time. Time is what they all want in the end. I have seen many a man stronger than Sarah beg at my feet for just a few more minutes, and yet I'd deny them. But something about Sarah, there was something about her I mean, I know you've felt it, she just has that special gift of persuasion, undeniable persuasion, and so we get what we have here....a barter of sorts." He smiled, swirling his glass between two fingers.

Thomas was back at the table, carrying a salad plate, tiny sprigs of greenery laying innocently in front of me.

"So as I said before, certainly an odd situation. I guess until Sarah can afford to pay her debt, you will be my welcomed houseguest. And I can assure you, you will be treated no differently than such. I am sure that you will find that despite my gruff exterior, I can really be quite a gentleman." He cocked a smooth grin.

Staring at my captor for lack of a better word from across the table, I began to see how he could be a gentleman, even a worldly man. His good looks gave him the confidence he needed to be a man of action, to be a man to be feared, even to be a man to be loved. I could see all these things in him, and I could even feel my heart fluttering at the thought of seeing this man's naked chest laying beside mine in a bed full of satin, his erect cock tickling my leg, us in our lover's embrace. All these things ran through my head, but then again it could have just been the wine talking.

I ate my salad quietly and half of the bloody steak that followed. After another glass of wine, I was following Vito out into the nighttime, his massive hand enveloping mine, my legs a wobbly and my head swooning. He led me out into his garden, dark bushes looming in the nighttime, unseen flowers kissing the air with their sweet scent. I followed him, one slippery stone step after another, his garden swallowing us, leaving his well lit mansion seemingly a thousand miles away.

Deep in the garden, we came to a humbly lit bench. He offered me a seat, and I crossed my legs as I accepted. He sat beside me, his eyes sparkling under the moonlight.

"So..." his cologne thick, his breath smelling of peppermints, "...what did you think of your first evening at my villa?"

I smoothed a strand of hair out of my face and smiled, "Lovely...absolutely lovely."

Vito reached out and pulled my hand away from my face, tracing my cheek with two delicate fingers as he did so. He caressed my hand, and stared into my eyes as if hypnotized.

"I...ah...." Was all I could say as his face lowered toward mine, his lips parted in anticipation.

My head swooning with alcohol and a little lust, I met his lips and opened my mouth to his invading tongue. His hand traced my thigh and ran along my slender waist. I reached out to him and wrapped my arm around him as we kissed in his garden underneath the moonlight. Our tongues danced and his exploring hand reached my chest, cupping my new tits, and I moaned in his mouth. My nipples grew erect, and I could feel my secret stirring between my ass cheeks. I pulled away, and his eyes locked on mine, his fingers still on my nipples.

"Is something wrong? I thought..." he began.

"Its not you...its just, this cant go very far." I lied.

"And why not? Are you telling me that it doesn't feel right?" His fingers had closed around my nipple and were teasing it above the fabric of my dress.

"Oh god no...its not that...its just that, well its that special time in a ladies month where....well."

He pressed a finger to my lips. "I understand. But there are other things we can do." He smiled coyly and stood up, my hand still in his, "Come with me and I will show you wonders you've never known."

I smiled and followed, my panties moist with anxiety.


Lying in Vito's bed with his satin sheets pulled up to my neck, I giddily waited for his return. I could hear him in the bathroom, clicking bottles around and unzipping unseen zippers. I waited, my naked chest heaving beneath the sheets, my smooth legs prickled with giddy goose bumps. My head canted on the pillow, following the sounds of unseen footsteps. He opened the bathroom door and smiled at me, the light behind him illuminated his naked body.

My eyes raced down his muscled chest and past his gorgeous six-pack abs, and rested comfortably around his crotch. I gasped, and he turned off the bathroom light, plunging us back into darkness. My heart was fluttering as he carefully climbed into bed beside me, his considerable weight shifting the bed. I reached blindly out in the darkness, and found his smooth face with a fingertip. He grasped my finger and thrust it into his mouth, sucking on it lightly. He pulled my slobbery finger away and yanked me up into his arms, his lips meeting mine, his hands expertly finding my soft nipples. We kissed as deeply as we had in the garden earlier, and in the midst of our deep embrace, I tickled my hand down his thigh and searched for his manhood, the very manhood that I'd briefly seen in the shadows of his bathroom. He moaned when my fingers closed around his growing shaft. I ran my fingers along the underneath side of his cock, tracing the vein back to his balls and back to the tip, over and over again as I felt it grow. He pulled away from my lips as he moaned. I closed my hand around the base of his cock, and pulled it all the way to the tip, applying pressure to the sensitive underneath portion. He moaned again, and his lips closed around my nipple. His tongue flickered, making points of my nipples. Sarah had been the only other person that had sucked on my new tits, but I had to admit that Vito might have had a little more practice at it than her. His tongue seemed to find all of the sensitive spots, all the nerve endings that flooded my brain with ecstasy. My hand began to work more feverishly on his swollen cock, and as I pulled and as he moaned, a crazy urge filled my head. An urge that I never would have even come close to having during my previous 20 some years of existence. I suddenly wanted, even needed to taste his cock. I longed to have my lips wrapped around it, my mouth salivated for it. So, I pulled away from him and disappeared beneath the sheets.

Face to face with it underneath the sheets, the true size of his cock was apparent. In that brief lighted moment it had looked enormous, just hanging limply against his thigh, and as it grew in my hand, I had felt that it was going to be quite large indeed. But as I lay underneath those covers, stretching my lips around it, taking it into my mouth, I thought I had never opened my mouth so wide in my life. And I took it in as deep as I could, but the base was elusive, I would gab before it reached my nose. So as I sucked and licked his massive member, I cradled his balls with my hand, teasing them. I heard him moaning above the covers and figured that I must have been doing a decent job despite my shallow throat. As I sucked and fondled, he began bucking his hips, trying to drive it deeper into my throat.

And then in the midst of it all, his bucking, my sucking, his moaning, he said something as he laid his hands on my head, stilling me.

I pulled off of his member, my saliva strings connecting us, "What was that?" I mumbled, that slippery cock looking more and more appetizing the longer I was not on it.

"I said, I have to fuck you." His breaths were short.

My heart skipped, "I told you...its my period."

"I don't care." He groaned, reaching under the covers, he yanked me up on top of him, our faces meeting once again. His eyes begged me. "I need you."

"Blood..." I mumbled.

"I don't care." He repeated, his hand tracing down my thigh.

I grabbed it inches before it found my crotch, my secret. "Wait..." I said. "I have an idea. Just lay back and relax."

"Very well." He mumbled, lacing his hands behind his head.

I sat atop him and turned around so that I was not facing him. I slipped my hands into my panties and freed my cock from between my ass cheeks. It stood straight out in front of me. I reached between my legs and grabbed a hold of his massive cock, aiming it up between my ass cheeks. I twisted my way down onto his lap slowly, inching his cock into my ass. I moaned and had to stop myself from masturbating as I did so. My own tiny cock ached and pulsed. I heard Vito moaning behind me as I stretched my ass around his massive cock, slowly lowering myself, slowly fucking him. And as he filled me, his cock stretching into me, a shuddered, my own tiny cock as hard as it could get. In that moment, as I rested my legs against his, him fully inside me, I felt whole. I felt like a real person again. I felt needed, I felt wanted. Suddenly, as I moved up and down his shaft, my ass swallowing it each time, I no longer missed Sarah. Vito started bucking his hips as I lowered myself down on him again and again, my ass cheeks slapping against his thighs, my asshole constricting and releasing, constricting and releasing. And then he erupted, shooting sum deep inside me, I could feel his cock pulsing inside and it was enough to send mine off in my panties.

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by Anonymous

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by Anonymous10/29/17

This was Great

I liked this story very much. It was exciting leading up to them fucking. I love anal stimulation

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