Winnie’s Chance

Read this particular entry from a female’s POV. More details available at the end of this entry.

Me: ‘Uncle Rick.’
Rick (whispering): ‘Shhh.. your mummy just fell asleep. Why are you still awake?’
Me: ‘Going to sleep now. Someone came over to look for mummy just now.’

He took the blanket away and opened my legs, rubbing my thighs in an uncomfortable way. It wasn’t the first time he entered my room when my mum was asleep, but he always visit her before he came over. So I assumed my mum knew he was here.

Rick: ‘Uncle bought something for you. Wear it for me to see?’

The then 16 year old me did not know what he was planning, and it was always those pretty clothes he bought for me. Those dresses that girls my age wear, and shirts and skirts that were always in the pictures of those blog shops I saw online.

My education stopped at secondary two when we moved out of our HDB into this condo, one that I knew my mum couldn’t afford on her own. My dad, who was totally capable of providing for us, got into some argument with mum and she took me with her when we left. Not knowing what happened, I just followed her and she gave me everything I asked for.

I took my shorts and panties off, in front of Uncle Rick and put on the black lacy thongs he gave me. It was a little ticklish at first, but after he showed me the photos he took while I was in it, I was fine with how it looked on me. My ass never looked so good with those cotton panties mum bought in packets of three.

He helped me remove my shirt and pulled a maroon coloured, cross-back, spaghetti top on me, snapping a few more photos after I posed for him to see.

The wide smile on his face made me happy, his eyes were all over me from top to toes. Frankly, I felt like the barbie dolls I always wanted when I was younger.

He placed me on the bed to browse through the photos he took and removed his own shorts. Since I had been getting naked in front of him, what he did did not bother me too much too. I’ve seen his little brother a few times. Whenever I saw his dick, my mind would be looking forward to the nice feeling that he would give me.

Climbing onto my bed, he felt up my legs again and pulled those undies off. His fingers went to my pussy and the pleasure tingled my head. He kept touching a sensitive spot and I could feel myself getting wetter. When he paused for a while, I knew he wanted my hand to be on his dick. He had guided me enough times for me to know that.

As soon as I was pumping his cock, he started moving faster. His fingers poked into my vagina and it was made wet when he entered. It moved in and out and all I wanted was for him to keep going.

My muscles stiffened up as he went super speed, making me moan with him. My pussy kept me shaking on the bed and before I knew it, a powerful sensation shot through my back, bringing me to a high. There was once he made me took a pill, and it felt the same. My mind was spinning and each thrust of his hand would introduce a soft, orange glow into my blurred vision.

I had to use his hand to please myself whenever he got tired, but his dick never left my hand.

Rick (whispering): ‘Want to try something new today?’
Me: ‘What is it?’
Rick: ‘It feels better than my fingers.’

Was it a toy? That vibrates? Or a second finger that I’ve never felt before? There was only excitement and none of suspicion I had for him. I had no doubts about anyone who showed care and concern for me. Yes, I was that naive. He spread my legs wider and sat between them. He placed both my hands on my stomach and helped me to open my pussy up.

He put the tip of his dick at my hole and leaned over me. It hurt a little when he forced my small pussy wide, but when he began to move in and out, the pain slowly went away. I felt him going deeper each time and my mind almost went blank when he was all the way inside.

It was so much bigger than his fingers and so deep I could sense my sensitive vagina hugging his stick. Cute, squishy sounds started coming out of where he was pounding, and it was way better than his hand.

I was half moaning and screaming, while he was grunting like a big bad wolf. To think I imagined myself to be ‘little red riding hood’ then, it was embarrassing.

We stayed in that position since I was too weak to turn over, and he just kept shoving his thick cock into me. Those colourful orgasms kept pulling me away from sanity, he was shocking my body with those tiny little climaxes.

Rick: ‘Mei, I’m going to cum!’
Me: ‘Cum?’
Rick: ‘Shoot something out. Like how you moan when you feel high.’
Me: ‘Oh! Then just keep going? I want Uncle Rick to be high too.’
Rick: ‘Cannot. It will dirty you.’

He took it out as my body recovered from an orgasm. He went around me to my mouth and I turned sideways to help him out. His hand went between my opened legs and continued massaging my sore clit, while I jerked him off.

My moans made him harder and he tasted my juices every once in a while. He was soon fingering me and I went faster till he held my hand tightly still on his dick.

Rick: ‘Open your mouth for me?’

Well, he licked me before in the past, so it was only fair I did it for him. He aimed his dick at my mouth and placed one of my hand on my pussy so I could masturbate.

Surprisingly, I was getting myself off easily and he was groaning louder. Suddenly, my body trembled violently to an orgasm and he shoved his dick at my lips. I sucked hard on them to keep myself from moaning too loud and a hot liquid splashed over my tongue.

It was warm and salty, and it kept coming. I was so worried my mouth could not hold all of it. After it finally stopped shooting, he squeezed his stick to get every bit out and his hand went back to my clit to rub me.

It was so comfortable when he did that and I just licked off all the white stains as he calmed me down.

Rick: ‘Let me see it.’

I pushed his cum with my tongue and he was in all smiles when some almost leaked onto my bed. He patted my chest and whispered for me to swallow, having only achieved that with some peaceful thoughts to ignore the eggy taste.

He took a few pieces of the baby wet wipes for me and we cleaned each other up. He wore his clothes back and I slipped the new pair of thongs on, along with my sleeping shorts. As for the top, I decided to wear it to sleep since it was so comfy and sexy.

Rick: ‘Can you tell mummy about this?’

I placed a finger over my lips and he placed a few blue notes on the dresser table for me. Only after two more occasions with Rick, I learnt that he had supplied my mum with drugs to keep her working (or sleeping). That was how he could get into my room my mum always warned him about.

At that age (of 16), I had no idea what I was being groomed into but it was clearer to me after I tried to Google ‘sex with uncle’. I found J through this blog. It has been almost three years since I knew the author, and only now, did I allow him to write my story for all to.. enjoy(?)

It is my past that is long behind me, and I no longer stayed with my mum in that dreadful ‘sex stop’ where more and more men came in and out I was spending more time outside than that ‘home’.

For my mum, she never moved out of the condo since the arrest of Rick never affected her ‘trading venue’. She’s probably earning more than me and has never bothered me more than those casual ‘how are you doing’ texts. I guess she knew how risky it was to be in that house where she worked.

Winnie now lives with two other girls whom I, J, knows went through similar ordeals. They were more than happy to take Winnie in to help with the rent-sharing. True story or not, it shouldn’t matter to you guys.

Although all things related to prostitution and freelancing should appear to be more professional now, there are countless unreported (small scale) cases where both lives overlap. I guess very few of us can picture ‘doing it for my children’ as a valid reason for them to sell themselves.

Yes, there are organisations set up to address that problem, but what if prostitution is the only way out? Have you ever cared to find out the truth? Or does it not matter as long as you paid?

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