A Scene From My Life

Addiction ruins your life. I had just turned 18 and was already 100K in debt, horses, sports, cards, you name it, and I had lost money on it. My current thought was to take myself to the top of a tall building, and a few seconds later, my problems would be over. How did Shakespeare put it? '...to die, to sleep, no more, and by a sleep to say we end the heartache...'

My bookie was greedy but not the slimy stereotype you saw on TV. He wasn't going to break my legs or arms or even kill me; you can't get fresh blood from a corpse; he just wanted his money, so he'd take my car, my apartment, and everything else of value. That day, he refused to take any additional bets from me, 'you're in too deep,' he said. 'You need to get square, and soon,' he gave me a card, white, heavy, excellent quality, very expensive, no name, just a phone number, 'try this,' he told me, 'it's a way out, you may even like it.'

It was intriguing, just a number, a mystery, daring me to call it. Hmm.

Her voice was very soft, pleasant, and sexy. I gave her my address, and she told me an Uber would pick me up in 15 minutes. Following her directions, I entered the doors to her office. The room was brightly lit and painted stark white with no decorations, no paintings, no company lettering, no receptionist, just two comfortable chairs.

She came in from the other door, tall, expensively dressed, and accomplished. I wouldn't say she was immediately pretty, but everything about her was well done and attractive; her walk stunned me; she walked with confidence and arrogance I could never manage.

She sat down and motioned for me to do the same, handing over the brochure in her hands. She still hadn't spoken to me. I read through it, wow, what the actual fuck.

'I service a particular type of client with a particular need.' Her eyes had mine gripped in confusion, doubt, and excitement. 'I can solve your financial problems, but first, you must be completely honest with me.'

I nodded.

'Are you single?'

'Yes'

'Are you a virgin?'

'Yes'

'Are you gay?'

'No.'

'Are you an orphan with no family?'

'Yes.'

The questions went on and on, all short, all yes or no answers, until finally.

'Would you like an explanation?'

'Yes.'

'I have a client who has a particular fetish; he likes to groom virgin sissies; you know what that is, yes?' I nodded. 'You fit his profile, right height, weight, figure, demeanor, and completely sexually inexperienced.' Well, she was right about that. 'It pays very well, and if you agree, it will clear your debts and leave you more than enough in the bank to start a new life. However, there is no backing down once the process starts.'

I was a bit startled by that.

'My client will be making a significant investment in you, and he's not the type to waste money; your bookie may not have had you tossed under a moving bus, but he will, do you understand?'

I managed to croak out a yes.

She handed me a card, the same as the other one, heavy and expensive, with just a phone number on it—a different number. 'Take tonight to think it over. Call this number with a "yes" or "no" at 9 AM. The Uber will wait to take you home. Don't worry; it's paid for.' She got up and walked out the door, leaving me in a silence of kaleidoscopic madness.

I didn't sleep that night; I spent most of it in the nook of my apartment window, looking out across the city and taking in the night's sounds. I had been suicidal that morning, and now I was just overwhelmed and confused. I had a way out; it was a pretty perverse way out, but so what? Sex was something I had never really considered as a thing; I thought of myself as asexual, neither interested in girls nor boys; bets were what turned me on.

Would this be so bad?

I called her number at 9 AM, 'Yes,' and hung up.

Another Uber was waiting to take me back to her office. It was transformed; there was a massive TV on the wall, racks of clothes, mirrors, a makeup station, and even a hair salon. Overnight, it had become a movie set. There was a buzz of activity; as young ladies moved around, she came in through the other door again, 'Come with me, sweetheart.'

First, I was showered, then shaved, completely shaved. Still naked, I was led to the stylist who dyed my hair blonde and then fixed it into a flowing, wavy breeze. My eyebrows were trimmed, and for the first time, I was made up. I could see myself on the TV standing naked; I thought I looked pretty. Then I tried on costume after costume. I never heard anything, but I could see that she did through the earpiece she wore; it was evident that her client was making the decisions.

'Stand still,' she ordered and then fitted a white chastity device over my cock. She was the first woman to ever touch my cock, it had started to stir, but she was an expert, and soon, I had the uncomfortable feeling of being locked into a white plastic cage.

She bent me over and fitted me with a small butt plug; I hated the experience, 'this is a lubricating device; when the time comes, you'll thank me for it.'

Then I was dressed: wearing a white floral summer dress with snap buttons at the front, white knee-high silk stockings, white panties with a red love heart on the front, and a matching bra. I was not ready for heels yet, so I wore feminine sneakers in white and pink. The dress was far too short; if I turned, it flowed with the breeze and gave an ample flash of my panties. It was sexy.

'White is for virgins,' she told me, 'this is the last day you will ever wear white.'

I looked at her, a little startled; last day?

'An Uber is waiting for you; it's a luxury car with leather seats; they are freezing. When you enter, hike up the back of your dress so your thighs are naked against the seat, and keep your legs open; the Uber driver will be able to see your panties, look at his mirror, and watch his eyes.'

She leaned in to kiss my cheek, 'Goodbye, sweetheart, or maybe it is just adieu.'

The driver opened the door, and I entered and did as I had been instructed; the chill on my thighs was unexpected but enticing; during the short drive, his eyes tracked to my well-displayed panties every few seconds. I was getting turned on by the lust I could see in them.

I was dropped off at the steps of a fancy brownstone townhouse. I rang the bell and was instructed to climb to the top floor. I knocked on the door and heard a harsh, 'enter.'

He came straight to me, took me in his arms, and kissed me; within seconds, his tongue was exploring my mouth. I didn't know what to do, but I had received some instructions; I put my hands behind his neck and stood on tiptoes, raising one foot slightly off the ground as we made out.

After a few minutes, he broke contact, stepped back, and said, 'Let me look at you.' I posed for a few seconds, then turned so my dress rose to flash him, 'Magnificent.'

He pulled me to him and, grabbing either side of my dress, tore it apart in one smooth motion to fall against the floor. I was startled, but I had no time to react; we were kissing once again, and this time his hand went into my panties to slowly flick my chastity device, then I felt their warmth against the skin of my butt.

This was all happening too quickly; I was semi-naked, being felt up by a man whose name I didn't even know. He expertly removed my bra and then led me to the bed I had avoided noticing.

We lay down, and with the help of his instructions, I managed to undress him; when I removed his boxers, his cock sprang to life, I hesitantly reached out to touch it, but his hand covered mine and dragged it over his throbbing member, I started to masturbate him, inexpertly, inelegantly, it wasn't something I had much experience with on my own to begin with, but he kissed my ears and whispered how well I was doing.

It wasn't long until I felt his hands on the back of my head pushing me down; I didn't resist, but when I started to kiss his chest, the pressure released. I kissed his body, slowly moving down; I knew what was coming; I wasn't avoiding it, hand, mouth, ass, what was the difference? In for a penny, as they say.

Finally, the glowing purple head of his cock was before my eyes; I kissed it and moved down the length, continuing to kiss it; he told me I was a natural; he was as hairless as I in that area; I took his balls in my mouth for a few seconds then moved up, back down, sucked his balls again, up, down, I was teasing him.

I opened my mouth to let the head enter; it didn't taste of anything; he was scrupulously clean; I bobbed a little, removed my mouth to suck air, then covered the head again. Little by little, I managed to take in more of the shaft. He was enjoying it.

'Good Girl.'

'A little deeper.'

'Faster.'

This wasn't so bad; I would remove my mouth and let my tongue flick at his cock, then let it slide into me again; he taught me to use my tongue when he was inside me to heighten his pleasure. It was a little messy; my saliva and his precum mixed and dripped down my chin, but the apparent pleasure he was taking from my very first blow job was exciting, stimulating, and erotic. I could hear him moan; his hands grabbed my hair, he was going to cum, and I was going to swallow.

He gave me a bottle of water to clean up with; then I lay beside him; his arms enfolded me and brought me into him. We didn't say much; after a few minutes, my hand reached for his cock, it was still flaccid after his orgasm, but as I played with it, it stirred to life.

He rose from the bed and returned with a large black cushion; it was slanted and had noticeable indents for a person'; legs. He explained that this was a device of his creation; it would position my pussy in the perfect position to give us both the maximum sensation and pleasure when we fucked.

I raised my hips, and he slid my panties off; I was now fully exposed to him. He began to kiss my body; I could feel my cock struggle within its plastic home as the pleasure and excitement overcame me. His hands slipped underneath me and removed the plug stuffed in my pussy. He maneuvered me onto the cushion; my legs were splayed at a 60-degree angle, with my pussy slightly above my head. As he moved between my legs, I looked down the length of my body to watch him pour lube over his cock; then, I felt him position his cock head at the entrance to my virginity.

He pushed inside me; I felt my pussy open to accept him; it wasn't pleasant, it wasn't painful, it was just different, then he pushed further and further in; it began to hurt a little; he was fully seated inside me now, I was no longer a virgin he told me, now I was a woman.

It was exciting; I could see only a small part of his cock, I knew the rest was stuffed in my pussy, and that turned me on.

He leaned forward to kiss me again, and I felt his cock move slowly back; then he pushed in again. It hurt more this time; he pulled back quicker and then thrust back in; he was starting to gain his rhythm. I had my hands behind his neck, looking up into the lust in his eyes as he moved inside me. He was withdrawing and then pushing the entire length into my stretching hole, bringing low moans of pain from me as the speed and harshness of his fucking began to increase.

We stayed in that position for a long time, the pain had faded ages ago, and the pleasure had taken over; I still didn't know his name, but I screamed in his ear, begging him to fuck me, don't stop, harder.

He warned me, which was nice, then I felt his warm spunk paint the insides of my newly abused pussy.

He stayed inside me for a few moments, then slowly slid outside of me. He gave me a washcloth to clean myself, and then I cleaned him.

'You did well; you'll get better as we go along in your training, but for your first time, that was very good; you're a natural.'

He pulled me back into his chest to cuddle, and I was content in the arms of this strange man. I didn't really know what had happened; it had gone so fast; it wasn't even 24 hours since I had called that number, and now my virginity had been taken, I had been fucked in the pussy, sucked cock, and my hands where once again stroking his member back into action.

'Turn around, bend over.'

I was stretched out along the length of his bed, my face buried in the pillows and my hands gripping the posts at the end. He was behind me, thrusting his cock into me, making me moan; at his instruction, I began to tighten and relax my pussy to his rhythm. He didn't come this time. Instead, he turned onto his back; I placed myself in position to mount him, found his cock with one hand and the entrance to my pussy with the other, then slid him effortlessly inside me. I rode him for about 5 minutes; my eyes were closed, and he was playing with my tits and flicking my chastity device; I desperately wanted to come; I was mewling like a kitty with the pleasure he brought me as he did.

Later as I once again lay in his arms, I complained about it; he told me to be patient he would release me in time, but for now, I had to concentrate on becoming the best fuck I could be for his pleasure, only when I mastered that, would we deepen our relationship into mutual orgasms, then he spread my legs and fucked me again.

As the Uber driver drove me home, I saw his eyes in the mirror, hungry. Addiction ruins your life, but sometimes it changes it, maybe for the better.