Caught Anal Masterbating

I started jacking off at the age of 12 and from then on I always had sex on my mind. I watched a lot of porn and about the age of 14 saw the videos of girls using dildo up their ass. I wanted to try it ask soon as I could find a suitable toy.

That summer I was home alone one day and came across my mom’s hair brush that had a long smooth handle. I stripped down, grabbed some lotion, and laid down on my back. I slowly slide it in. It hurt but I kept going. I had about 2 inches of the handle in me. I stopped and jerked off until i came. I cleaned it and put it back.

I thought about it for the next week and decided I wanted to try to get it all the way in (about 5 inches). The next day I stripped down and started. It hurt but after a while I had the brushes pushed against my cheeks. All of a sudden I hear a noise. I look over and there is mom. She screams and I pull it out and drop it. She yells at me the entire evening about respecting her stuff.

Comments

Anonymous

by Anonymous on Apr 25, 2025 at 5:28 PM

Did she buy you your own dildo?

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flexflesh65

by flexflesh65 on Apr 25, 2025 at 7:11 PM

Unfortunately no! I wish she would have…

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Anonymous

by Anonymous on Apr 29, 2025 at 7:51 AM

I did the very same thing as a young boy. I used my fingers for awhile but wanted more so I looked all over the house and like you I found a hair brush with a long handle it was sort a flat small at both ends but very wide in the center.
I used Vaseline and it took me awhile to get it in my ass. It hurt once I got to the really wide center part of the handle but once I got that in my ass it slipped right in and it was stuck up my ass and it felt damn good. I laid there stroking my hard dick then got up to go look in the mirror at it sticking out of my ass.
As I walked the brush pricked my ass cheeks and the handle stayed way up inside of me. Once I bent over and saw my ass in the mirror I got excited. I walked all around the house for the longest time stroking my hard dick and pulling on the brush from time to time and it felt so good I laid on my bed and jacked off then used my fingers to gather up my cum and lick it off my fingers. I left that brush handle up my ass for hours and I jacked off so much my dick was sore. I ate my cum every time and by the end of the day I was exhausted and my asshole and dick hurt.
After using the brush handle several times i started to experiment with a lot of other things around our house and I was amazed at just how much I could stick up my young ass.
Some things I tried just hurt too much and were way too big for me to get in my ass but I sure wanted it. We lived at the edge of town and there was this big wooded area there so I spent a lot of time there naked hidden in the thick brush using long neck beer bottles in my ass because my dad drank beer and the bottles were very easy to get and no one ever missed them. I could only get the neck of the bottle up my ass but it sure felt good and I would fuck myself and jack off every day several times a day.
One day I didn’t hide good enough and I was naked squatting down over a beer bottle fucking my ass when I heard something and when I looked around this older boy that lived close to us was standing there with his pants down hacking off watching me fuck my ass.
As soon as I saw him I froze scared to death and he told me to keep going. So I did as he told me then he told me to stop and stand up so I did. He grabbed me turned me around pushed me to the ground and told me to be quiet and then he told me it was his turn
I laid there naked in the leaves and grass and he forced his big dick up my ass then told me to shut up and told me he was going to fuck me and if I told anyone he would beat the shit out of me.
He fucked me really hard with his big hard dick stopping several times then starting again. Then he got all excited and told me he was going to cum and he was going to cum up my asshole. He came with his big dick all the way up my ass and he wasn’t finished.
Hs huge naked body on top of my young naked body felt good and he started to fuck me again and right away I felt his cum all over my nuts and it was all over my ass and thighs as he fucked and fucked and fucked me some more. It took him the longest time but he came deep in my ass again then his dick got soft and slipped out of my asshole then his cum poured out of my ass.
Once he stood up and started to get his clothes on he asked me if I lined it and I told him it felt pretty good. He laughed and then said good because I am going to fuck you every day and you better be here after school or I will kick your ass.
For weeks I waited there naked for him to stop by and fuck me and leave me with an ass full of cum. One day I waited for him and I heard him coming but he was talking to someone and he had another boy with him and I was scared to death.
They got up close to me then started to take their pants off and both of them were hard and he told me they were both going to fuck me and his friend had a bigger dick than his and they both fucked me twice and left me there face down in the grass with cum pouring out of my ass.
It happened often and he even brought other boys as time went on then one day he showed up with a black boy and after he fucked never black boy fucked me and they took turns on me for a very long time
One day while he was fucking me he made me suck on this other boys dick and he came in my mouth and held on to my head pushing his dick in to my mouth until I swallowed his cum. Once he made me do that it was normal for me to get my ass fucked with a dick in my mouth.
After several years of him and his friends fucking me all the time he went into the navy and we moved away but all thru the years I haven’t several select hung men fuck me in hotel rooms when I was traveling with my job.
I still use toys and my wife loves to strap one on and fuck my ass she really gets off fucking me and she likes using big cocks to fuck me. I get very horny at times and I still like to get naked in the woods and fuck myself and we have property out in the country and on occasions my wife and I will take the strap on toys and we get naked outdoors and she loves to fuck me out in the woods.
I have been waiting for her to tell me she wants to watch me get fucked by another man but she has never mentioned it. I know she wants that but won’t ask me to do it. I would if she asked and I think about her under me in a 69 while a man with a really big dick fucks my ass and shoots his load up inside of me as I cum in my wife’s throat and she squirts all over my face
She loves toys too and a few times using two strap on dicks she has got two in my ass at the same time and she likes to test my limits as far as thickness and depth.
She also enjoys tying me to the bed face down to use toys on my ass and she can play for hours and I enjoy it also.

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