Sister Caught Me Dressed

781Report
Sister Caught Me Dressed

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.

Similar stories

A Fuck-Bike for Wendy

Wendy smiled as they passed the starting field. The sun was already blasting down on the busy crowd, colorful shirts and nervous chatter overloaded her senses. Thanks for doing this, Luke! I'll make it up soon. No worries, Wendy. Just let me win this time. No chance, sweetie. You'll see my backside from start to finish. As always. Then I demand a compensation fuck afterwards, he pouted, his eyes sparkling with lust. With pleasure, Luke, with pleasure. Let's find a place to park, we have only 10 minutes left. Are you sure you'll manage the 50 miles this time without embarrassing...

864 Views

Likes 0

Taking Sarah,Part Two

Taking Sarah, Part two Help from a friend. Over the few weeks since I had taped Sarah in the bathroom, I tried numerous times to view her again, to no avail. I did have one opportunity to view her close-up quickly. She had fallen asleep on her bed, the top bunk after school one day and Anne called upstairs that dinner was ready and would i wake Sarah. Entering her room i saw that indeed she was fast asleep. As i approached her I saw that her shorts were very loose on her. I knew that if i just moved them...

759 Views

Likes 0

Sam & Alicia 9

I have written this assuming that you have already read Sam & Alicia 1 to 8. When I woke up next morning, Katrina was propped up on one elbow looking at me. She looked happy. “Good morning sleepy head. Did you sleep well?” “Yes, I slept like a log. You look happy. Would you like another fuck?” “Yes, I feel very happy. I should be shocked by all the things that I learnt about you all last night, but I'm not. Instead I feel proud that you have included me in all your sex. My parents would be horrified if they...

692 Views

Likes 0

The Wood

It was cold. I lay hidden behind the bush close to the grassy path lining through the dark wood, it was my fifth night waiting. Often times a man or a group would walk past, but that wasn't what I was here for. It wouldn't be long - maybe tonight would be my night. I sat patiently, eager for the sound of footsteps. I checked the time... 12:54.It seemed quiet for a change. But then I heard the rising sound of faint footsteps followed by the crack of a few twigs. Then I seen her. Down the path to my right...

630 Views

Likes 0

Trained to serve

I was in my bedroom upstairs while my parents were holding their annual New Years Eve party down stairs. The only bathrooms were upstairs and the guest bathroom was just down the hall from my room, so I heard people coming up and down the stairs. I had just put on my pajamas and was sitting on the side of my bed looking at ads in Popular Mechanics when the bedroom door opened. It was Mrs. Smythe who lived across the street. She was wearing a tafata blue dress that was tight, showing a rather voluptous body. I could smell alcohol...

1.4K Views

Likes 0

The New Shed

I was building a new workshop and needed some help. I called four friends who had carpentry skills and were regular meetings for me. We all knew we were sex partners but we kept things discrete since none of our wives knew of our extracurricular activities. The concrete for the floor had already been poured by two very energetic gentlemen, but that is another story. The lumber had been delivered a few days ago along with all the hardware. The saw station was set up in a shady area so work could go quickly. The wives took all the children to...

1.4K Views

Likes 0

Dominated by her

I was 16 at the time and was not a V, i often went round my friends house to drink and have fun. At first his much younger sister did not appeal to me but after she started walking about the house in tight leggings my attention slowly moved on to her toned fine figure. Her panties showed though her tight leggings that gripped the round the shape of her peachy ass. She was well developed for her age and whilst wearing a low cut top i was able to have a quick look down there. But these quick glances were...

993 Views

Likes 0

The Lesbian Debt (Chapter 5) - The First Mayim Sessions

Chapter 5 THE FIRST MAYIM SESSIONS Laura went to the toilet near the end of the work day and took the pills she'd been given by Dr Windred. They reminded her of how horny she'd been this morning, a horniness that she'd never satisfied, and for a moment she thought about locking herself in a toilet stall and jilling off. But she didn't trust herself to masturbate at work without being caught, and anyway Amy had told her not to play with herself before turning up at the clinic. So she just left work, her pussy already wettening. Erica still had...

950 Views

Likes 0

A Trip On My Own Pt. 2

Hey Everyone, Well, Part 2. I was on the wall for hours or so it seemed. It was making me sore to be there with my legs spread and I was having to pee but thought I may not be allowed. Finally the woman that had put me there came back and slapped my tits hard making me cry out. God, ready little bitch? she said with a growl in her voice. Yes Mistress, I am ready. I told her. Well, we will see, but now you have no choice. She said and put a blindfold on my face so that...

851 Views

Likes 0

The Lips, the Teeth, the Tip of the Tongue_(1)

Just the tip.. okay love? you almost beg. Not long ago, she showed you that a blowjob does not have to involve deepthoating. You see, this was something she was taught by her best friend Ashling. The skills were passed to your wife to help her confidence.. 'Thank you Ash.' you repeat since hearing the story. Ever since, you craved for the the oral skills of your lover, the adorably shy Kara that you met so long ago. She was a classmate, teased and harassed but you stood up to the bullies for her. You showed her how to punch and...

827 Views

Likes 0

Popular searches

Share
Report

Report this video here.