Debt and Repayment

It all started about a month after I arrived in New York. It was an old story, I guess - the small town girl who finds her way to the big city to find fame and glory as a dancer, a musician, or, in my case, as an actress. I had the passion, drive and talent to make myself a success. Growing up, I had never wanted anything else. As a child, I had starred in every school play, participated in every church Christmas pageant, and waved from every parade float as a harvest festival princess. And I had the looks to open a few doors along the way. I'm 19, 5'7" and fit, with long legs and nice 36C tits. I also have naturally red, curly hair that I wear long, and big beautiful blue eyes. Not the look for every part, of course, but hard to ignore nonetheless.

I said my goodbyes to my family and friends, assuring them that the next time they saw me, I would be a successful Broadway actress, and made the long bus ride to New York, arriving with nothing more than a suitcase full of clothes and a bit of money I had saved up waitressing. The money went fast - I was shocked how expensive things were - and after just a few weeks, I realized I should have come with more of a plan.

At each audition, I found that I was just one of hundreds of beautiful, talented young women, many of whom also had years of acting classes, voice coaching, and previous roles to boast on their resumes. I got a few callbacks, but not one single job. Soon, I was faced with the fact that I'd either need to go home and admit defeat - never! - or find another way to pay the bills as I waited for my big break to come.

Rather than spending my last 20 bucks on something practical like food or rent, I made the regrettable decision to try my luck at a little gambling. There was a pub in my neighborhood that was well known for its poker on Saturday evenings, and I figured I didn't have much to lose - my older brother had taught me to play back home, I knew the rules of the game, and I was a good enough actress to pull off a bluff when it mattered. What I didn't know about myself until it was too late, unfortunately, was that I had a tendency to be a bit compulsive when it came to gambling.

Things started off well, as I found myself sitting next to an attractive older man who introduced himself as a producer and bought me a steady stream of drinks as we played. His name, I learned after it occurred to me to ask, was Vinnie. He looked to be about 40, and was 6' tall with an impressive, athletic build. His dark Italian looks were complemented by his gorgeous suit, and his charm, combined with the alcohol, quickly won me over.

I won a few hands, was up about 100 bucks, and then started my downfall. I lost everything in one hand, but fortunately Vinnie spotted me some cash so I could keep playing. This is where my gambling problem became apparent. Just as soon as I was up again, I would lose everything, not knowing when to stop or hold back. By the time the night was over, I owed Vinnie $400. I was too naive at the time to realize he had taken advantage of my obvious gambling problem, and was grateful to be in debt to him rather than some of the other players at the table, who were, let's just say, less friendly.

"Don't worry, Julianne, you'll pay me back in time. In fact, I'll give you a shot right now to cut your debt in half. I'll flip this quarter - heads, you owe me another $200, tails, I'll take $200 off your debt."

"OK," I said, stupidly agreeing. Of course it was heads, just my luck.

"Hmm, OK, I have another idea," he said as we walked out of the pub. "I'll take $100 off if you come back to my place and suck my cock."

I was shocked by his forward proposition, but also intrigued. He was hot, he was charming, and I probably would have gone home with him anyway, debt or no debt. I told him as much, and he just smiled, replying, "We're close to my place, follow me."

We barely managed to shut the door to his apartment once we got there, because I had my arms wrapped around him and he had his tongue shoved down my throat. This was not a sweet seduction, this was rough lust: we quickly tore each other's clothes off and tossed them aside as he pulled me towards his bedroom. Following through on my promise, I quickly went to work on his cock, which was already half-erect by the time I pulled it into my mouth. He immediately grabbed me by the hair to guide my motions as I worked his shaft in and out of my mouth.

As he grew bigger, it was soon obvious to me that Vinnie's cock was much larger than that of my high school boyfriend - my only previous blow job experience - and before long, he was pounding into my throat. The last thing I remember before I apparently passed out was the gagging feeling as Vinnie groaned and shot his load deep into my throat.

When the morning light woke me and I found myself alone on Vinnie's bed, two things quickly became apparent. First, that he had me in quite a vulnerable position: either pay off my debt to him, or go home with my tail between my legs, admitting I had failed to become a star. And second, that I had been right about Vinnie. He was charming. He was a gentleman. Well, OK, he was a guy who would take advantage of a young woman's weaknesses to get sucked off. But, that said, he hadn't taken further advantage of me that night. And he had made me a delicious breakfast.

Over that breakfast, Vinnie and I had quite an interesting conversation. You see, he had developed quite a plan, one that went well beyond just paying off my little debt to him.

"So, Julianne. I learned quite a bit about you last night. You're headstrong and determined, but you're also naive. You're adventurous and passionate, but also inexperienced. You're compulsive, and don't have the humility you need to make it in this business. And, you still owe me $300, even though you haven't got a penny to your name."

"Uh huh," I responded through a mouthful of bacon and eggs.

"So, I've got a proposal for you. Keep in mind, you're free to say no, figure out another way to get me the $300 and then get out of town. But if you really want to stay here and make it, I hope you'll consider it."

"Oh, yeah, I don't want to give up yet. What do you have in mind?"

"Well, you proved yourself quite well with that spectacular blow job last night."

I blushed, put down my fork, and he continued.

"I'll let you out of your debt if you join me in two more sexual encounters today - of my choosing - consider them worth $150 a piece."

"OK, I'm listening."

"Then, you can choose to leave, I'll never bother you again and you can go back to pursuing your New York dreams on your own. Or..."

"Yes?"

"Or, I'll put you up here in this apartment, and help you make some connections in the business. But those favors will also need to be repaid, if you know what I mean."

"Hmm... OK, well, I'm up for the first proposal, and then why don't we take it from there?"

"OK, as long as you understand that you have to do exactly as I say, and I'm not going to tell you anything about these situations in advance. Giving up a little control would be good for you, I think."

"I get it, debtors can't be choosers. When do we get started?"

"Meet me back here at about noon. Come prepared for anything."

I left his spacious apartment and found my way back to my own crappy place, which was paid for only one more week. As I thought over our conversation and the situation I found myself in, I felt a strange combination of emotions. I was embarrassed, I was a bit scared, but I was also excited, both about the mysterious sexual encounter awaiting me, and also about the potential of this relationship for my career.

After showering and choosing an attractive outfit from my meager selection, I made my way back to his apartment at the appointed time. I rang the doorbell, knocked, and rang the bell again before a woman finally answered. She was strikingly beautiful, tall and dark, and wearing only a bra and panties, stockings and heels. "You must be Julianne, please, come in." The woman, at least 5'10", took my hand and led me along the same route that Vinnie and I had taken the night before, winding around a few tables and chairs and into the bedroom.

"Get undressed and lie down," she commanded, authoritative but also gently feminine. I knew the situation was such that I couldn't question, couldn't take the time to doubt what was happening. For a moment, I wondered where Vinnie was, but let that thought go out of my mind just as quickly as it had arrived.

As soon as I had completed my task, and was lying naked on Vinnie's king-sized bed, the woman climbed on top of me, holding something against her chest with one hand. The way she covered me with her body prevented me from moving, and it was soon obvious why she wanted it that way. She let her hand fall from her chest, and several long strips of silk fabric fell against my chest. One by one, she used them to tie first my hands and then my feet to the bed. I didn't fight against her, but did instinctively test the bonds, and they were firm enough to keep me from moving, but the silk fabric was quite comfortable against my skin.

I had never even imagined that I would find myself in a situation like this. Any fear I might have felt from finding myself in such a vulnerable position was quickly washed away by the pleasurable feeling of the air touching my now-exposed pussy. The woman left the room for just a moment, then returned, again climbing onto the bed next to me. Without a word, she began caressing my breasts in her hands, and I couldn't help but writhe in pleasure, straining against the fabric that held me down. After a few moments of this, she replaced one of her hands with her mouth, gently nibbling on my nipple and suckling my breast as her hand moved down to my pussy.

Already dripping as it was, she was able to quickly wet two fingers and push them into me. I was not a virgin, but could still easily count the number of times my pussy had been penetrated, so she found me to be remarkably tight. Again, I attempted to writhe beneath her, but my motions were so limited that I was completely at her mercy. She was still suckling my tits and thrusting her two - wait, now three - fingers into me when I heard Vinnie's voice in the room.

"That's enough, Sonya. I don't want her to cum until we're ready."

Sonya - I finally knew her name - pulled away from me instantly, and I groaned in disappointment.

"Oh no, Julianne. Don't groan. Show a little patience. You'll have your pleasure - just remember that it's on my terms."

I nodded as humbly as I could, and waited to see what would happen next. Vinnie climbed onto the bed with us, positioned himself between my legs, and began stroking his half-hard cock against my soaking-wet pussy lips. He motioned for Sonya to join us, and she began sucking the tip of his cock and occasionally brushing her fingers against my clit as he continued to grow outside of me.

Before long, he was ready to enter me, and I braced myself for what I was sure would be a slight bit of pain. I closed my eyes and bit my lip, but he surprised me by entering me very slowly and gently. Even though I had never had such a big cock inside of me, Vinnie's slow stroking allowed my pussy to gradually expand to take him in. The feeling was so incredibly erotic - so much better than my high school boyfriend randomly thrusting himself into me with no regard for my need for at least a few seconds of foreplay.

As Vinnie started to fuck me, Sonya positioned herself over my mouth, facing him, and I realized that I was going to taste a woman for the first time. She slowly lowered herself down to me, and I reached out my tongue her clit, gingerly at first, and then, responding to her motions, with more confidence. I wanted to use my hands, and struggled more than once to get them free, but Sonya just responded by grinding her pussy down onto my tongue, and using her own fingers to stroke her clit.

I was soon overcome by a wave of feeling unlike anything I had ever experienced. I couldn't breathe - both because my face was buried in Sonya's hot, sweet pussy, but also because Vinnie was now pounding my own pussy with such force. And the inability to move or control anyone else's motions was surprising in its erotic force - something that I would have imagined to be frustrating was instead satisfying in that it forced me to release control.

Vinnie began talking to Sonya, asking her if she was ready to cum, asking her if she liked watching him fuck the same young hottie who was eating her out. Sonya couldn't respond in words, just in grunts and groans as I released all of my own passion directly into her pussy. At that moment, she stiffened above me, and my face was covered with her juices as she came. "God, Vinnie, that was fabulous," she said to him as soon as she had recovered. "I really want you to give it to her now, pound her until you shoot your load into that tight little pussy of hers."

I was so ready, so incredibly turned on by her orgasm and his continued fucking of me, that I couldn't hold on any longer. Even before he came, I had my own orgasm, my pussy pulsing around his still-thrusting cock. It was by far the longest orgasm I had ever had, and I was still enjoying the feelings rushing through my body when I felt him cum deep inside me. Once he had finished, he quickly pulled out of me and released the silk ties on my hands and feet, allowing me to stretch and relax into a new position.

"OK, sweetie, you rest here for a little while. Then, I want you to take a shower, put on the clothes I've laid out for you over there." He pointed to a chair in the corner of the room. "Then, use one of these silk ties as a blindfold, and wait for me here on the bed. I'm going to leave with Sonya now, and I'll be back in a few hours with someone else."

Exhausted, but now incredibly excited for whatever Vinnie had planned for me next, I carefully followed his directions. The outfit was a cheerleader's uniform, short pleated skirt with matching v-neck sweater, both ridiculously tight. There were no panties or bra, which I assumed was a deliberate oversight on his part. After I had put on the clothes, I did find two hair ties which matched the fabric of the uniform, which I assumed were meant for pigtails to complete the look. After allowing a bit more time to pass, I made my way back to the bed, put on the blindfold as instructed, and sat down to wait.

As I waited - time definitely moves more slowly when one is wearing a blindfold! - I thought back over everything that had brought me to this place. Rather than feeling any kind of resentment, I was happy to have found Vinnie. I thought back to our conversation that morning, and decided that if the next $150 encounter were anywhere near as good as the first, I would take him up on the rest of his offer, and fulfill any sexual fantasy he could dream up in exchange for the nice roof over my head and help in getting a foot in the theater door, so to speak.

Finally, I heard the door open, followed by two voices - Vinnie and... another man! Of all the scenarios I had imagined he might have planned, this wasn't one of them. As thoughts raced through my head, their voices came closer, and I heard the sounds of shoes coming off and clomping to the floor, followed by the less distinct sound of other clothes gradually being shed. Were there really two naked men in the room with me, and what exactly did Vinnie have in mind?

"Sit up, Julianne. Suck on this for a while." As soon as I was upright on the edge of the bed, Vinnie's now-familiar cock was in my mouth. Just as I had established a rhythm, bobbing up and down and enjoying the sensation as he grew in my mouth, he pulled out and said, "Now, this one!" And now there was a new cock in my mouth, a little smaller in girth but clearly longer: only half-hard, it was already reaching into my throat. Again, I worked towards a rhythm, fighting my gag reflex as this longer, thinner cock stroked my mouth.

The two men kept this up for a while, alternating a chance at my mouth, tugging on my cute pigtails as they fucked that orifice, soon both rock-hard as I fantasized about what other orifices they might want to penetrate. Almost as soon as I had the thought, I felt one of the men join me on the bed, pull me back down until my head hit the pillow, and push my legs apart. Expecting a cock, I was pleasantly surprised when I instead felt a tongue on my clit, and then stroking back and forth on the outside of my pussy lips. The other man - Vinnie, I soon learned - pulled me towards the end of the bed so that I could go back to sucking his cock while I was pleasured orally.

"I think she's ready, Vinnie, and I know I am" said the other man as I wrapped my legs around his head and pressed myself into his face. I could feel some of my juices trickle down onto my leg as he pulled away from me. This other, mystery man was now lying down on the bed, and pulled me on top of him, positioning me, still blindfolded as I was, over his cock. I took it from there, taking his cock into my hands and guiding it into my waiting pussy as I let my weight fall onto him. I loved the feel of his long thin cock inside of me, and quickly began bobbing up and down on him, relishing the sensation of depth that he was able to reach. He slowed me down a bit by reaching under my cheerleader's sweater and grabbing my tits, but I still rode him with enthusiasm.

"OK, my turn!" I heard Vinnie say as he climbed onto the bed. The two men pulled me off of one cock and onto the other, and I resumed my rhythm as quickly as I could. As I fucked Vinnie with abandon, I felt the other man get off the bed for a moment, and then return. I could sense him behind me, but didn't know what they had in mind, and frankly, was enjoying myself too much to care.

Vinnie now pulled me down from my upright position into an embrace, and slowed our pace dramatically. He reached down and pulled my cheerleader's skirt up as far as it would go, and now I felt the other man's hand on my ass. After a couple of firm slaps, I felt something cold hit my skin, and soon realized that he was massaging some kind of lubricant into the skin around my asshole, working in smaller and smaller circles until his fingers actually began penetrating my tiny virgin ass.

Vinnie had slowed his motions inside of me to almost nothing, so that all of my attention was now focused on this man's fingers. I felt something press against my tiny hole, and just as I had prepared myself for the thought of one finger entering me, I realized it was his cock. He thrust deep into me with one well-lubricated stroke, and I cried out with the initial pain and shock. Both men held still inside of me until they felt my pussy begin to pulse again with desire. Vinnie started first, stroking a few inches at first and then soon with all of his length. Once that rhythm was again established, the other man began moving inside of me as well.

I didn't last long in this scenario, and collapsed against Vinnie's chest, whispering in his ear, "Yes, yes, yes." Over and over again, 'yes' was all I could utter as these two men fucked me and I experienced the most powerful orgasm of my life. The two men came within just moments of each other, pushing me to new levels of delight as their cum shot deep inside of my two holes. The three of us stayed in this position even after we had all finished, not wanting to let go of the incredible sensations.

Soon, though, both men pulled out of me, and rolled me back onto the bed as they climbed off. "Just let us get out of here, Julianne," Vinnie said, "and then you're free to take off your blindfold. And remember, you're free to leave now, or welcome to stay, it's up to you. I'll be back in a few hours, so make up your mind, and I guess I'll find out your decision when I get back."