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My first hands free anal orgasm

My first hands free anal orgasm

I would like to premise this by saying that I have dildoed my ass on several occasions and sometimes felt nice but others quite... well... not so nice. this time i did it right and I may never go back...

I had gotten home knowing i had a surprise in the mail. I had ordered a set of 10 Variety panties and thongs and... a dildo. This was probably my 4th or 5th that I've owned but i keep purging. Anyways i was excited when i got home so much that my clothes practically flew off of me after i walked in the door. I opened the package and laid out my new panties and thongs to see what i had received, all of which i cant wait to show off to you. but there was the other package i had ordered which was a pretty basic looking dildo... nothing too big but i could stick it to the wall if i liked. Excited by trying out my new item i hopped with the dildo in the shower and rinsed off all the while sucking at it like it was the man i was itching to have his semen down my throat. i rinsed out my ass and hopped out. Dried off and threw on one of my new panties. omg i felt so sexy. combine that with putting on my huge breasts and my red curly wig, my head was spinning with anticipation..

i threw a towel on the bed. opened my laptop and threw on a playlist of sissy hypno videos. grabbed my dildo, a rather large vibrating butt plug, lube and last but not least, my new bottle of poppers. I laid down on my side and took a big whiff of poppers and i was off.

I started slow with the dildo just to make sure i wasnt going to be hurting but when i got comfortable oh boy it got good. i felt every thrust go deep in me and loved ever inch. After a few minutes of pounding my asshole and making it loose, i figured i would give my still new butt plug a try... Even with my sissy pussy loosened up it was still a tight fit. but finally i got it in... this was a first time and i tried out the vibrations but couldn't feel them.. turned it on high and still was dissatisfied... finally i had enough of it. it took a few painful minutes but i finally got it out. I stuck a few fingers in my ass to feel around and realized i could fit 4. Woah... I have never been that open before, but as i explored i felt it... A sudden wave of intense pleasure rocked my body as i knew i had found my sweet spot. i tried to keep going but realized that it was too hard to keep up that awkward angle.

HOWEVER... i realized if i positioned the dildo in the right direction i could hit it every time and OMG DID I HIT IT EVERY TIME!!! It was pleasure as i never experienced. I slamming that dildo in my ass while my limp sissy clit twitched helplessly. Faster and faster as the tension built up. Took another hit of the poppers to drive me wild. I kept going faster and something deep in me was blowing up like a balloon of built up orgasm till finally. AHHHHHHHHHHHHHHHHHHH. The dam of pleasure gave way as I came in a way i have never before. I couldn't believe it. I had finally done it. I scooped up my cum in my hand and swallowed every bit of it i could in victory. I sat there as i caught my breath and realized that i may never be able to cum the same way again.

In a afterthought, my arm is really sore... i hope that sometime in the future i would be able to go all the way and see how a real man feels in my sissy pussy.

Toni <3
Published by redheaddynamo
3 years ago
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46
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twitchums
i loved your memory of your first sissygasm.  I would love to give you your next sisygasm.  You're a cutie.
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jojosmallone
love having hands free orgasms both from either sucking cocks or getting butt fucked. The best part is my tiny penis never get erect
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jayymie
Sheer bliss the first time it happens :heart:
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megahurtz68
Now that is a great story! 
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YuiMinami
Amazing!
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Fred-the-Great
Sexy bitch! I’m impressed. And near Chicago…
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funtimez2bhad
I'd love to probe your p-spor with my stiff pecker!
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Amazing experience!! Love how you described your thoughts! I’ve had the wonderful pleasure of the same p spot orgasm a few times. I was in chastity and wasn’t hard. It seems to take the right toy, the right frame of mind, and that certain hunger. Truly amazing! Thank you for sharing!
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I have had lots of toys with no luck cumming with just toy's. So I guess that I will have to find a real cock to do the job, I think that will be a lot more fun. 
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Janedoecd2
what a great description, there still is hope for me
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I know the right angle, u should relax and hit the prostate. Tension hides the P-spot. I did it in my sissyboy ass
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 best feeling. I love every time it happen
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xx1236
You did  it right by loosening up your anal canal first..After that there is only pleasure left..AA++
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singlman
I I know how to find the little slut hidden in you dear Toni
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PNWgirl
Hot! I've yet to do this. I've tried an anal dildo but it was too tight :frowning: Somehow a real cock is easier!
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singlman
To bad you are not be my neighbor? You will not have to use anything other than my thick stiff dick to relieve your pussy on fire my little slut
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Reev_starr
All good for you! Did you go all the way and felt how a real man feels in your sissy pussy since?
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lustybixy
Great story ?
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prairieFreak13
Great story Toni! and thanks for the add!~kisses~Bri
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That is fantastic! I'm so jealous. I bet you get cock very soon, you're gorgeous!!!!
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Once you decide too allow a real man inside you please share every detail
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36karramba
Awesome
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pussyriot420
Fantastic!
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Been there and done that you are hooked now you will forever be getting  bigger and bigger dildos until you get a real cock and then you'll never be happy with your dildos anymore.  Good luck.
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tyedyesissy
to redheaddynamo : You do not get facial irritation that way?  Check this place out ARTISANALCLEANERS.COM Possibly lower case, very fresh
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That was so sexy.    
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Dickme122
Ive had it happen only once (so far) : ). It was amazing! And now i know ill be chasing that feeling forever.
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knighthockey16
Welcome to the club.
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redheaddynamo
to tyedyesissy : actually i have recently taken to putting some on the disposable masks and wearing them... holy crap it gets you feeling out of your mind.
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tyedyesissy
I get so close but then strength goes out of me and never get there. so I made a fuck machine and now I stop it or pull off because it is too intense, so I envy you. Do you put your poppers in a water squeeze bottle?
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