Pay for Pleasure – Prequel

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I had written about how Sandy turned me into a $50 whore before writing about how I got to that point with her.

I was cruising an online posting for sex one Thursday evening and I came across a posting for TV looking for big cock. Well that got my attention, I’m 8″ and very thick.

So, I shot a reply right away. Not a minute later Sandy and I started chatting, we hit it right off. Although I was inexperiences with a TV girl we were into a lot of similar kink.

We made arrangements to meet later that night at her place.

When I got to Sandy’s I found her even sexier than her description. She was is 6’1″ (6’4″ with heels) thin and muscular with a tall lanky thin swimmers body. She had read lipstick on with a red wig. She made me feel right at ease and I immediately fell under her spell.

She got me very comfortable and soon we were both naked on her living room floor as she was sucking my hard cock and I was exploring her nice round ass.

After about 15 minutes I needed more, I wanted that ass, so I rolled her over and found she was already nice and lubed up. She raised her ass to me and I slid right in. Sandy was a great fuck, she knew what she wanted and she got it. She was not very tight, she obviously had been fucked a lot and as I would find out, not just by cock. We fucked for forty-five minutes, doggie-style at first then on my back and finally as she was laying on her back with her 7″ cock staring right at me, I knew I had to have that!

Now, I’d never sucked a cock or been fucked before, but something about Sandy was different, something made me want her.

So I went for it, first I started to stroke her as I fucked her ass then I just went for it, I pulled out tried to slide my ass on to her cock.

Sandy stopped me and asked what I was doing.

I said. “I don’t know, but I want your cock.”

She said not today, “You are here to fuck me.”

I replied with, “Yes mistress.” I’m not sure why I said that, but it seemed to turn turn a switch in both of us.

Sandy told me “Fuck me hard and cum.” I started to pound her ass as hard as I could, slapping her ass and pounding my hard cock into her deep wet cunt. I came so hard shooting hot cum in and out of her ass. It was all over her. It felt wonderful.

It was then when she first asserted her dominance over me. She told me “Lick it off me.”

I immediately did without questioning or debate. I was licking my own cum off her hot well fucked ass and out of her cum dripped cunt and loving it.

When we were done she asked, “Do you wanted to be fucked.”

I said, “Yes, but I’ve never been fucked before.”

She said, “Come over Saturday night and we will change that.”

Saturday couldn’t come fast enough. It finally came and when I got to Sandy’s she was waiting for me. This was to be the first step in my conversion from a top to a bottom sissy whore. She had on a red wig, black skirt, black pantyhose, a tight black top hiding her perky breast cups and a riding crop.

What did I get into I immediately thought.

I was told, “Strip in the entry way and crawl to me.”

I stripped naked and crawled to her. She preceded to slap my ass with her crop, my balls and my back too. This is not what I agreed to I thought. She then explained to me what was going to happen, I was going to be her sissy whore. I was going to be her sex toy. She explained to me I was to do what she said as she said or I would be punished. Again, I thought, this isn’t what I wanted, but I couldn’t leave. Sandy had me under some sort of spell.

After I agreed to her terms of submission we proceeded onto my first bottom experience.

Sandy ripped open her pantyhose and ordered me to suck her cock. She forced me to what at the time seemed like a huge monster down my throat. I tried to take as much as I could I struggled and gagged against her aggressive thrusting, but I eventually found a rhythm. I was sucking my first cock, I was loving it and not doing too bad a job.

Sandy was saying things like, “Take it slut,” “Swallow that cock,” “Suck me you whore.”

She would ask me things like, “How do you like sucking cock?” “So you want to be my sissy whore”, “You want to be my pathetic cunt?”

It was all turning me on and I wanted to fuck her again and I wanted to cum, but she would have no part of it. Her hands never left the back of my head as my mouth received her hard thrusting cock.

After what seemed like an hour but was maybe twenty minutes of cock sucking she stopped and took me to the bathroom saying She wasn’t going to waste her cum in my mouth tonight. She said I needed to be clean before she would fuck me. She handed me an enema kit and said, “Make sure you are clean or else.”

I of course did what I was told. I was in a cloud, I couldn’t think straight, but I couldn’t stop.

After I returned to the living room Sandy ordered me onto my knees and started to finger my ass. It felt good, but I was very tight and very nervous.

After Kurtköy Anal Escort a few minutes I think I wore out Sandy’s patience and she said, “I’m going to fuck your virgin cunt.” She said if I was to be her whore she would fuck me raw. Again, my brain was saying no, but my body said yes! I couldn’t say no to her and I just met her.

She lubed up and started to force her hard cock into my ass. It hurt like hell, I screamed in pain. Thankfully she stopped for a minute and then we started again, this time slower. After a few short slow thrusts she was inside me. It was both pleasure and pain. To have this hypnotic t-girl fucking me was unbelievable, but my ass was already starting to hurt and it had only been a few minutes. Sandy preceded to ride me from behind, slapping my ass as she pounded her smooth slick hard cock into my ever welcoming virgin hole. I was suddenly her whore, her slut, her piece of ass. This was all imagined and more.

Sandy then stopped, I was hoping she was done, because although I was enjoying the mental state of being hers my ass felt like it couldn’t take any more. She then put me on my back pinned my legs back and pounded my now exposed ass even deeper and harder than before. The pain would not stop, but we both didn’t care. She enjoyed breaking me in and I enjoyed every thrust and every hard painful pounding inch of her rock hard cock.

Sandy would speed up, then slow down then speed up again until she just kept going faster and harder and then she pulled her cock out of my ass and told me to open my mouth.

With a couple strokes she shot her hot, wet, seed all over my face and mouth.

“Taste my cum you sissy whore,” she said. “Taste it and lick it up.”

I did, I couldn’t get enough of her. After what had seemed like hours I finally had what I wanted. I had Sandy’s cum and I was hers.

I knew there was no turning back, I felt like a dirty whore. I felt pathetic, used and my ass was on fire, but I wanted more.

Little did I know in the weeks to come how much more I would get and how truly pathetic and dirty I would become.

These events are from my memory and in hindsight the details get a little fuzzy. In this second story I will describe my time of intensive training with Sandy. These event are somewhat graphic and may be more psychological than sexual but they are clearly both. Again, sorry if its not overly sexual.

I arrived at Sandy’s one evening unsure of what to expect after our previous encounter. As before, I immediately stripped as ordered. I was a little nervous and I cant explain why.

The feeling of being owned by Sandy was undeniable but something was holding me back. She had every intention of fucking me and I had every intention of letting her, but it hurt this time, and I mean really hurt. Maybe we fucked too hard my first time, I don’t know, but she would force her cock into me and I would fight it. I believe I was fighting it both mentally and physically. I didn’t just want to give myself to her I wanted her to take me to truly own me. To know that she could dominate me mentally and physically. To know she was strong and I was weak.

So I told her, “This isn’t going to work, you just might have to rape me.”

I needed to know what it was like to take it even if I didn’t want to. To have to look at her and know she stripped me naked and took away and the dignity and pride I had.

I wanted to be raped and I needed to be raped to make my submission to her complete.

So there I was naked on Sandy’s floor telling a taller stronger t-girl who had fucked me and owned me that I wasn’t going to get fucked and if she wanted it she needed to rape me.

She took me and there was nothing I could do to stop her. Sandy pounced, before I knew what to do, Sandy had me face down and she was on top of me. She was trying to grab and control my wrists. I was struggling and fighting back. I really honestly was. I was saying, “No” and “Stop, I don’t want it,” even though I needed it.

I was trying to squirm away but she was too strong. Sandy managed to get her knees inside mine and push my legs apart and said, “You will take it you dirty whore.”

This really limited my ability to move and she now had control of both wrists. All I could do was pinch my ass together and move it as much as I could. I continued this for as long as I could, but eventually I was broken, she had my wrists, was on top of me and I couldn’t move.

She managed to get her cock inside my ass enough that my simple shaking couldn’t move it. “I’ve got you now you pathetic piece of shit,” she said.

It was then I realized I had lost, she was stronger and my will was broken. I can’t say I enjoyed what followed, it was painful and I hated myself the entire time, but I didn’t fight it.

I took it like a whore and just wanted it to end.

Sandy pounded my ass and said, “You are my pathetic weak sissy.”

She asked me, “How it feels to have your ass raped and you Kurtköy Yaşlı Escort cant stop me.”

Now my ass belongs to her. It hurt, it really did, but it was also what I needed. I needed to be broken, to be put in my place to know she is the boss. I’m just her pathetic sissy whore I thought.

She then, without warning, added insult to injury and came in my ass. This is the only time she has ever done that.

As she started to cum she said in a scolding tone, “Take my cum you pathetic sissy” as my ass filled with her seed and telling me “I’m fucking serious you weak pathetic cunt.”

I know knew how serious she was.

When it was over she knew I would be back, I said I didn’t know if I could see her again, but I knew I would be back. I was hers and I needed her strong cock and strong hand to guide me.

I was back of course, my next visit to Sandy was at 2:00 am during the week with instructions to get naked in my car and walk to her building.

What kind of pathetic pussy would agree to this humiliation? Well I did of course. I got naked in my car then ran across the parking lot to her apartment building. I knocked on her door and of course waited naked at her door to be let in.

Once I got in I was treated to even more humiliation. I had no idea what to expect, but after the events of earlier that week I knew I would do as she instructed me. Sandy immediately ordered me into her bathtub and to get on my knees. She walked in wearing only a bra and carrying her digital camera. She really meant business tonight. She was going to exert her dominance over me.

She simply stood over me and pissed all over my rock hard cock, my chest, face, and hair. My mouth and eyes were closed, but I could feel the warm pass splatter across my face and body. I could hear her say how good the pics would turn out.

What the hell are you doing I thought, but I was frozen, I couldn’t move. It was like I was paralyzed by her. It wasn’t humiliating enough to be pissed on and not do anything about it, but to be photographed too. What was I thinking, I was hating myself but I couldn’t stop.

After taking her pictures Sandy left and told me to shower and clean up.

I did as told and after my shower I found I still had my raging hard on.

Of everything I have ever done the following is my most pathetic moment. I crawled to Sandy who was sitting on the couch and begged her to piss on me again, I wanted to taste her. Yes, I wanted her piss in my mouth.

I asked her, “Mistress Sandy, I want your piss in my mouth, I can’t get enough, I need more.”

I needed more humiliation from her.

She told me to get her a water from the kitchen and to get back in the bathroom and wait.

I sat in the bathtub naked, cold and wondering What The Fuck was I doing and why couldn’t I stop!

She eventually returned and said, “Open your mouth and get ready.”

So she took out her soft penis and preceded to tease me with it by slapping me across the face with it and calling me a pathetic sissy, a sorry humiliated pathetic worm. I was her worm.

Sandy then gave me what I wanted she took her penis and placed a foot away from my mouth. She started to spray my face with piss then adjusting her aim to fill my mouth with her warm piss. It was more than I could swallow, it was running out of my mouth and down my body. For the second time in an hour I was a dirty whore bathed in Sandy’s hot piss.

When she was finished she said she was done with me for the night, and told me to get dressed and leave without cleaning myself off. No shower, I cant drive back covered in piss I thought to myself! Sandy said, “You are a pathetic whore, a worm, and that is how you are to be treated.”

She was right, that is who I was and although I hated myself at that moment, she gave me what I wanted, what I needed, the most humiliating night of my life.

Shortly after my most humiliating night of my life Sandy gave me the most wonderful fulfilling night of my life.

After my last encounter with Sandy, I didn’t know what to think. I knew I was owned by her, I couldn’t escape thinking of her, even after our last encounter where I was left to drive home drenched in her piss.

So it was with some severe hesitation when I opened the door to Sandy’s a few days later. I entered, stripped naked and crawled to her in the living room.

When I got to the living room I discovered Sandy had her digital camera a tripod and lights set up, obviously for photography shoot.

Sandy informed me that we would be taking pictures of my transformation to a sissy whore.

A sissy whore? This was exciting! I always loved Sandy’s smooth legs, her smooth body and her feminine scent. I was going to be a girl just like her.

Our first step was to shave my legs. Off to the bathroom we went, where just a few days earlier I was a pathetic pissed on worm, but today I was on my way to being a sissy!

Sandy told me to sit in Kurtköy Zenci Escort the tub and she took the shower head and washed my legs with water and a very flowery body wash then she applied shaving cream to me legs. She applied having cream all the way up to my pubic hair. She said it was all coming off.

I was expecting to do all this myself, but Sandy wanted to make sure it was done right and was afraid I would cut myself. Sandy also wanted to capture this by taking pictures of my progress. There I was, my legs covered in shaving cream, my cock hard and Sandy capturing it all. After the slow deliberate but delicate process of shaving my legs was completed Sandy told me to shave my cock clean and smooth and to shave my chest.

By me shaving my pubic hair and my cock it allowed Sandy more time to capture me becoming a Sissy. She would order me to turn to get a shot of my cock or of my ass or whatever she wanted. I was in a fog of happiness. When my legs, cock and chest were good and smooth, Sandy rubbed lotion all over my body. She had such an amazing loving touch that evening. She was making me feel like the whore I wanted to be.

Next was makeup, she applied makeup on me for the first time. Red lipstick of course, eye liner and eye shadow, base and blush. Not too much of anything though, she didn’t want me to look like a tramp or too slutty. She had other ideas for me tonight. Lastly I was given a short blond wig to complete me. When we were done with my makeup, I was amazed, I looked good! Good for a sissy whore of course. We then went to the living room where Sandy had my outfit all spread out. First I saw a short plaid schoolgirl skirt, a little white short sleeve button down shirt, a lacy black bra, matching black panties and white thigh-high stockings. Wow, I thought, this is for me, I cant wait to put it on! But Sandy stopped me and told me she had other plans for us. To start with she took pictures of my naked body, my ass my still hard cock, my freshly shaved legs.

She ordered me to my knees and told me to suck her cock. I gladly did as I was told. Sandy was wearing her customary black. Black fishnet stockings, black leather skirt and black leather zip up vest and of course no panties. She looked hot! Her ass was magnificent and her tits were huge! I took her cock from under her skirt and wrapped my red lips around her cock. It was a wonderful feeling, to be under her sucking her beautiful hard cock. I took her cock deep into my mouth rubbing the base with my fingers and sucking hard and fast. All the while I was enjoying her cock she was taking pictures of me from above. My red lips taking her cock in my mouth, me licking the head, licking the shaft, every thing I did she captured.

Then she took one hand and started to face fuck me harder and faster. She told me, “Don’t make a mess of your makeup so swallow.” She let out a moan and said, “Take my cum you whore, you cock sucking whore.”

And I did. I felt her warm sticky cum fill my mouth and throat, I swallowed every drop and sucked what ever I could off her hard cock before letting it escape my mouth.

After pleasing her it was time to get dressed. Sandy had a plan, first the panties. She took pictures of me sliding my panties up my legs, my hard cock stuffed inside lacy black panties, and the way the panties curved my round ass was so hot to me.

Next was the bra, followed by the stockings. I was told to stop along the way to make sure she got just the right shot. I was her sexy cd slut model.

Next was the top, it was very sheer and you could easily see the lack black bra through the top. With the implants Sandy gave my, I had nice perky breasts.

Lastly was the skirt. It was so short, it didn’t cover the top of the thigh-highs. It didn’t cover the bottom of my ass. I couldn’t believe how short it was, but I loved it. I had to pin my hard cock up against my stomach to hide it from popping out from the skirt.

Sandy then took pics of me in many positions. It was so hot, I felt so slutty. I still had the taste of her cum in my mouth and I was showing off for her. She complimented me on how I looked.

She said, “You are a real cum sucking whore now.” “You need a name though,” she said, “Ill call you Pleasure.”

I assume she had put thought into this because she instantly announced the name Pleasure.

Sandy then told me to follow her to the bedroom. When we got there I discovered Sandy had wrist and ankle restraints on the bed.

She told me, “Lie down” and she strapped me in.

I was totally helpless. I was at her total mercy. She took more pics of me like than then she went to her closet and pulled out a thick 10″ dildo and told me to suck it. Here I was strapped to a bed with a huge rubber dildo in my mouth. I was loving it and so was Sandy.

By this time her cock was nice and hard again. She unstrapped me and told me to get on my hands and knees on the bed. She started to massage my legs, ass and cock. She pulled my panties off and took more pics, focusing on my tight little cunt. Behind me I could hear but could not see that she grabbed some lube and a butt plug. I felt a cool sensation filling my hungry yet tight pussy. It felt great! It was smaller than Sandy and fit like a glove. Sandy took more pics of my exposed ass.

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