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What was your first anal insertion?

mthomson2020

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For me, it was a well lubed penis. Never got into putting something in myself, though now I've discoverd my prostate and I do that sometimes
 

D_Ghana_Whey

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I believe for me it was my fingers, if not that then a hairbrush handle.
 

Pandasaurus

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smooth toothbrush handle (did not use that toothbrush again)

That's also when I learned...I'm not into anal.
 

BigSexynine

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proactiv bottle (small size like prob 3-5") and a 3.5" long by 1" diameter flashlight. Boy it doesnt look that big BUT it sure feels huge when its up there lolz
 

scotty661

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My wires rabbit vibrator when we were first together she left it at my house and I was already pretty curious. Wow it hurt at first but after it was in....... Hmmmmm good stuff one of the best orgasms to date
 

oralslut464

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I was at my grandma's house and was sneaking around my cousing bedroom - I was 13 he was 18 and found a long rubber dildo - looked like he had made it himself - not a professional one - took it into the bathroom and found some cream. At the time I didn't know the cream was menthol cream. so I lubed up the dildo and shoved it it. WOW what a sensation. I had to wash real good to stop the burning. UGH. It left an impressionn to say the least. After that I used to get condoms and fill them with piss - tie them off and put them up into me and jack off. Loved the warm feeling of the piss in the condom and the pressure up my ass. From then on I found a friend in Jr High school and he would fuck me - until he moved.
 

D_Louisa May Alclit

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A former lovers cock. He thrust it up there without notice, which wasn't cool but it hooked me on anal.
 

SR_Pepe_LePube

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It must have been my fingers - all I remember that it was a glorious sensation when I discovered prostate masturbation.
 

Alkaz

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Regular cucumber with a condom on it. Managed to get about 3/4 of it in my 14 year old self. Never managed to get as much in me since which I find very odd!
 

B_Nia88

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my mom's hair brush with a large round handle when i was 11 dreaming about my Daddy's coworker.
 
A

AM_092

Dad: "Where did the batteries in the remote control go?"

Me: "I'm charging them."
 

xxxllover

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For me it was a very big penis when I was very young. At least I think it was very big but it was so many years ago that my memory might be corrupted. What I am certain of is that it hurt like hell. I am surprised that it didn't put me off being fucked for ever.