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Introduction:

Caught cross dressing by my hot little sister.
PLAYING WITH MY LITTLE SISTER

My name is Jamie, I was only 5 when Dad had left so it was just me, mum and my sister, Amy who is 2 years younger than me.

I was 12 when I started wearing my mothers underwear
It turned me on as I progressed through puberty and help me achieve bigger orgasms. I progressed to wearing bras and suspender belts and stockings under my everyday clothes and I loved it.

When I was 14, mum decided that I was old enough to look after my sister when she went out. Sometimes she worked in the evenings and other times went to the cinema or theatre with friends. My sister did not know I wore mums underwear. She was entering puberty herself. Her tits were growing and she was a 34b (I’d been through her underwear when I was alone) and she seemed to be more aware of sexual things
One evening we were watching television, mum had gone to the theatre, and I was wearing my usual bra, suspender belt and stockings under my clothes. I soon became so hard that I had to relive myself. I told my sister that I had to go upstairs and went to my room. I took off my outer clothes and began to wank in front of the full length mirror.

Then the door flew open and my sister, Amy was there.
“what are you doing?” I shouted.
“well I certainly know what your doing but I didn’t know you were such a pervert, wearing mums underwear.”
“well you shouldn’t be in here looking, go downstairs.” I said
She replied, “ well I don’t know why you have to come up here if you come down as well I can help u .”
I was a bit shocked by this, I didn’t know what she meant by help me but I wanted to find out so we went downstairs.

I sat on the sofa and Amy sat next to me, my cock was rock solid and stood up to attention it’s head glistening with sweat. Amy took hold of it lightly and began rubbing her fingers up and down the full 6. ”I’d never felt anything like it, it was so different to when I touched myself.
She rubbed faster and grabbed harder and I felt my balls filling with cum and tried to hold back. I told her to slow down, which she did and the feeling eased. Then she bent over and kissed the tip of my cock. Some pre-cum seeped out and she licked it up, then she began sucking the head of my cock. I couldn’t believe the feeling , a tingling all over my body, I couldn’t hold on any longer.
“ I’m Cumming.” I shouted and she moved her mouth away just as my cum spurted 2 ft in the air landing in her hair and on her face, the second spurt was almost as big and Amy made sure she was in the way of it. After the 6th an final spurt Amy’s hair and face was covered in my cum and she was smiling.
“oh my.” she said, “now that was a cumshot brother you are the champ.”
“You mean you’ve seen other boys cum?”
“of course, I didn’t learn to wank and suck like that overnight.”
“ so what you make a habit of sucking cocks at 12.”
“oh I’ve been doing it since I was 10. It’s amazing what a boy will do to feel like I make him feel.”
“you mean you take money for it.”
“ Money, presents I don’t mind.”
“So my 12 year old sister is a prostitute, a whore.”
“ I prefer cum slut, but yes same difference.”
While this conversation had been going on Amy had been licking my cum from where she could reach and scooping the rest with her fingers, into her mouth. She opened and I saw her mouth full of my cum, then she closed and with one swallow the cum was gone.
“mmmmmm “ she said, that was tasty.
“so how much will that cost me “ I said sarcastically.
“Oh I’ll do you for free any time if you can cum gallons like that.”
“Great “, I said, “Will you do me another favour?”
“What’s that?” she said
“ Next time can I cum in your pantie drawer?”
She smacked my leg and said, “Oh you really are a pervert but you’re my pervert.” she kissed me full on the lips and I had the faintest taste of my cum still lingering on her tongue.
So that’s how it started. The next time mum went out Amy was the first to start she took off her blouse and bra and began rubbing her nipples. I took off my top clothes to reveal a pink lace overbust corset, pink silk panties and pink stockings.
“Oh don’t you look sweet.” said Amy, “that looks ready for action.” she said indicating my hard cock inside the panties.
“ you’ve got lovely tits,” I said, “ can suck them?”
“ ok.” she replied sitting herself next to me on the sofa.
I leant over and sucked first one nipple then the next. Amy whimpered and reached down and touched the outside of my panties. My cock seemed to grow even more and she moved her hand inside the panties and pulled my cock out and began wanking me. I put my hand on her knee and slowly slid it up her mini skirt until I reached the edge of her panties.
I hesitated but she said,” Go on, don’t stop.” so I eased my hand inside the panties and found the juicy lips of her warm pussy. I eased one finger between the lips and pushed it into her hole.
I was reluctant to go too deep, she was only 12 after all so I just rubbed her lips and clit but this was enough to have her moaning in ecstasy.
She moved her head towards my cock and took the full length deep in her throat.
Oh fuck I thought what am I doing as I eased my finger deeper in her cunt but that was the last doubt I had as the cum rose in my cock. I held it back and eased another finger into my sister she wriggled and moaned and I held on.
I rubbed her clit and she sucked harder on my cock. She squealed as she came on my hand, the juices pouring from her virgin cunt and I yelled, “ I’m cumming.” as I shot my load in her mouth. She sucked it down and each spurt after until I was spent. This time when she kissed me she passed some of my cum with her tongue and I swallowed it down. Oh heaven I thought as I lay back in the sofa with Amy on top of me and her tits on my face.
I was determined that no matter how much I wanted to I was not going to fuck Amy. She was too young.
But it was difficult holding myself back especially when she was so precocious. When I told her why I wouldn’t fuck her, it was just a signal for her to tease me relentlessly.
But for the next 2 years I held out until a fateful evening in November when mum had gone to the theatre.
Amy was now nearly 15. She had matured spectacularly and her figure was now 38D 24 36 and her hair was waist length auburn and glistened especially in the right light. She was a stunner.
That night she sat me down and began to speak more seriously than usually.
“Jamie.” she said. “ I want you to fuck me tonight, I have to lose my virginity.”
“why?” I said, “You don’t have to do anything.”
“you don’t understand, jonathan has been pressing me to sleep with him and I want to say yes, but I want you to be the first, so please.”
Jonathan was amys’ boyfriend and I liked him and I could understand why she wanted to go further with him, he was a16 yr old rugby player all muscles and testosterone.
Against my better judgement I said,” ok.”
She threw herself at me and kissed me full on the lips. I was slightly put off because there was the underlying taste of cum and I knew it was Jonathans but it was me she had come to to lose her virginity so I would make it the night of her life.
She said she was on the pill now so we could go ahead and she continued to kiss me deeper and more fondly, her tongue caressing mine and my cock hardened with every flick of her tongue.
I said that we should do it in bed and she said, “ Mums big bed would be great.”
“Ok” I said and I took her hand and led her to mums bedroom
When we took our top clothes off we were both wearing identical underwear. Black Bra, Black suspender belt, black stockings and black panties. I had some false breasts in the cups of my bra which made me 38c so we were almost identical.
“Spooky.” she said and lay on the bed.
I lay next to her and began to caress her leg just above where the stockings finished.
She released my cock from the black lace panties and squeezed my balls, I pulled down her panties and stroked her cunt lips and eased my finger onto her clit.
She whimpered again and stroked my cock. I eased my hand behind her and undid her bra and she did the same for me.
We stoked each other like we’d never done before and kissed deeply.
I pushed my hard cock against the lips of her virgin cunt and entered her gently. I went deeper and broke her maidenhead with one thrust. She cried out and held me tight as I went deeper and I began to fuck her properly.
She was moaning as I sped up and she continued to moan and then screamed as she came at the same moment I emptied my load inside her beautiful cunt. Oh what a night.
We slept but too long the next thing we knew our mother was standing over us with a strange look on her face.

To be continued
13 comments

Anonymous readerReport

2014-01-01 02:11:56
totally DUMB you have to warn the readers when adding shit like crossdressing loser.

anonymous readerReport

2013-06-30 16:53:30
fouck i whish my sister would do that

anonymous readerReport

2012-03-21 16:53:17
between the cross dressing and her having a boyfriend both kind of ruined the story. why would he want to fuck her if it was just so she could fuck someone else she just proved she didn't really love him just wanted to use him. he should have told her no and avoided her forever

Anonymous readerReport

2009-10-24 18:45:09
nah....pretty lame....

buntyReport

2009-10-16 18:48:00
american keep it up

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