Having my own place was giving me the freedom to spend all my free time as Chloe, that changed when my sister asked if she could stay for a week as her place was having some building works done. My sister is a few years older than me average looking and single.
Having her stay was limiting my dressing time and meeting people but it was my sister and she needed help. As we were having a meal, she cooked she told me that she would be going out with one of her friends and that she would be staying overnight.
What a chance I had and decided there and then that would be spend the evening as Chloe and spend the evening dressed and on cam and chat with anyone who wanted to chat.
When she had left with her overnight bag, I raced to get dressed to make sure I got every minute I could after spending a few days in male mode. I dressed in a matching lacy bra and panties, suspenders and stockings. High heels and a dress that came just above the knees.
The wig I chose was a long black straight haied one, and make-up and got myself in front of the webcam. I went into a chatroom, and nothing was happening on the cam or in the chat room, so I turned it off and decided to watch television.
It must have been about midnight i was sat there dressed when I heard the key in the door! Before I had time to hide or even think, my sister had now walked into the room. I must admit she looked hot in her little black dress and heels dropping her bag.
She spoke asking where her brother was and then I registered that she was looking at her brother dressed and was stood there staring at me.
She looked to me and said, 'what the hell I thought you were my brother's girlfriend?' I didn't know what to say. I told her that I had been dressing for a while now and all I wanted was to look and be treated as a woman then came more questions which I answered honestly.
She'd had a few drinks and decided she come home as her friend had a family issue that and she couldn’t stay over. She told me to stand up so she could see me in all my glory, I did as she asked.
She laughed at me but then said the best words I've ever heard! ' You look good for a second I thought you were his girlfriend”. This was not the reaction I expected but it made me feel good.
We chatted some more, and she asked if I had met anyone while dressed, I told her I had, and she said “looks like we enjoy the same things” I looked at her then she said “Cock we both like cock” I mouthed yes, a bit embarrassed about it telling my sister that I had sex with men.
Next day before she left for work, she told me that she expected me to be dressed when she got home and during the day my mind was spinning wondering what she expected and what was going to happen.
I was ready for her when she got home, I could tell she was impressed by the big smile on her face. She went upstairs to the bedroom taking her bag with her and shouted me to come upstairs.
We were in my bedroom. She told me to take the dress off so she could see me in my underwear. Standing there in my underwear and “keep your heels on' she said.
She took her dress bra and knickers off and was now naked. I was shocked my sister stood there naked and she looked good even though she carried a little extra weight.
Then she started to walk towards me. My cock was already hard. She grabbed it and kept calling me a naughty boy but wanking me hard and fast at the same time.
As our foreplay progressed, we moved onto the bed where I laid her on her back and started sucking lightly on her right nipple. My left hand found its way down to her pussy it was then she stopped me what had I done wrong but she got up and picking up her bag went to the bathroom.
In she walked wearing a huge strapon dildo and joined me on the bed I snuck a finger up behind the harness to her clit and began massaging it gently. I didn't want to overstimulate her too soon. She soon began moaning and squirming under me as I pleasured her nipple and clit simultaneously. It was obvious that she was enjoying herself.
Suddenly, almost as if flipping a switch, she pushed my head away from her breast and commanded me to suck her cock.
I was somewhat taken aback by her sudden change in demeanor but I followed her dictate and dropped to my knees on the side of the bed. A real cock has a man attached to it with feelings and feedback. A dildo is just a cold chunk of rubber that transmits little or no feeling to its wearer.
I started timidly by licking the head of the dildo with my tongue. It was cold and tasted funny. However, I could see that my subservience gave her great pleasure so I continued.
Sucking on a dildo isn't nearly as good as sucking an actual warm, hard cock but I tried to put on the best show I could for her. She was really getting excited and started barking orders at me:
"Suck that cock; it's nice and hard for you! You like sucking cock, don't you? Yeah, that's it! Suck it hard. Get it in your mouth. That's it “Suck it like you mean it and if you do a really good job of sucking my dick, I'm going to fuck you like I know you want it”.
That was all it took to get me really into sucking on the dildo. That drove me crazy!
After I got the dildo good and warm and wet she commanded me to stand up in front of her.
She sat up on the bed and took my hard, throbbing cock in her mouth. She was an excellent cocksucker and took me as deep down her throat as she possibly could which heightened my arousal even more.
After a few quick sucks on my dick she told me to lay down on the end of the bed with my legs spread.
I quickly did what she asked me to and before I knew it she had some lube on the end of the already slick dildo and she was working it over the length of the shaft with her hand, all the while giving me a seductive eye.
"I'm going to fuck you now I'm going to fuck your ass like you want me to, you little slut. You loved sucking my cock so much that now I'm going to give it to you in your ass. “Just wait until you feel the smooth, hard cock plunging into your ass. You'll be squirming and begging for more”.
With that she walked up to me and guided the head of the dildo right at my ass. She took one slick finger and started pushing into my asshole which got me to focus on relaxing.
My head started swimming with pleasure as my sphincter relaxed and welcomed her finger inside.
It felt so amazingly good for her to stick her finger inside of me. I started riding a wave of pleasure that was indescribable.
She could tell that my ass was relaxing and getting ready for her dildo. She withdrew her finger and started pressing the head of the dildo into me. The head popped in with a little jolt.
I was so horny that I was almost shaking. She pushed the rest of the dildo into me in one quick motion. There was a momentary twinge of discomfort but that soon subsided behind the incredible pleasure coming from my ass.
She started her fucking slowly by drawing almost all the way out of me. Very gradually she began picking up speed.
Over the course of a couple minutes, she worked her way up to a respectable fucking tempo and just settled in there.
Her hands were on my knees pushing them back into my chest as far as she could. She was leaning her weight on me as much as she could while she was fucking me.
The sight of my sister fucking my ass with a strap-on was absolutely the hottest fucking thing I had ever seen in my life! I was so delirious with pleasure at that moment that I would have agreed to anything.
It didn't take very long for me to orgasm. Her fucking was thorough and rigorous. The buzzing from the vibrator in the base of her dildo was hitting me with each thrust and hitting her clit sending her into a spiral of ecstasy. All at once the feeling of her fucking sent me over the edge.
My ass and balls started to spasm uncontrollably as she continued pounding me.
The cum shot out all over my chest and abdomen. To that point it was the hardest I had ever cum in my life!
She could tell that I was done so she pulled her rubber cock out of me and laid down on the bed next to me.
We laid there for about ten minutes while I recovered from the intense orgasm. She slid off the harness and took the dildo into the bathroom to wash it. I laid there with my loose, slippery ass still relishing the amazing fuck I had just been given by her.
When she came back into the bedroom we chatted, and she told me that I was going to be her fuck toy and that it was to be our secret and that she had plans for me.