Anonymous Confessions

Over 40,960+ Anonymous Confessions Shared!

Do you have a secret from your past that you've been dying to share?

This category is all about unburdening yourself of the confessions you've kept hidden since childhood. Share your tales of mischief, rebellion, and discovery. Whether it's a forbidden crush on a teacher, a prank gone wrong, or a stolen kiss with a childhood friend, this category will take you back to the innocent and rebellious days of youth.

- Childhood Confessions -
Straight Male / 24

I Was Frequently Milked By Momma

I grew up with my mother in a trailer park in eastern Ohio close to the West Virginia border. My mother was single, my father saw me from time to time. As a little boy I rested my head on my mother's lap to watch tv. She would slip her hand into my pants and play with my penis. As I grew older she would 'milk' me before bedtime. She never jerked me off, it was a warm hand on my penis, as I got erect she milked me slowly until I lost control. She cleaned me with tissues and kept my penis in her hand until it was time to go to bed.

I was around fifteen when she stopped, telling me I needed to find a girlfriend, get a blowjob, get some pussy. Getting a girlfriend like that was not so easy and I resorted to self milking, which just made me hornier. I did find a girlfriend, and she does blow me and she likes to fuck, but getting her to just milk me while we watch tv is not something she wants to do. Knowing my mother milked me only makes it worse.

3
# 46089 - by Anonymous
    • - Childhood Confessions -
    Straight Male / 41

    When I was 12 I went to Boy Scout camp with the other 6 scouts in the troop. We were accompanied by the adult troop leader who was in his 40's.

    Since we were to be there for a week we were required to shower every evening before we went to bed. The adult troop leader always supervised us to ensure against horseplay, or so he said. Turns out he was looking for a sexual victim. Four of the other boys were only eleven, and the other kid who was 12 hadn't reached puberty. That left me, as I was already in puberty, with a 3" penis and a solid band of pubic hair around the base.

    One night it was very warm in our cabin and everyone was sleeping in their shorts. Late that night I woke up to find the troop leader rubbing his hand on the front of my shorts. I said nothing. He then slowly began to pull my shorts down. Once again he started to rub penis, and when it started to stiffen he wrapped his fingers around it and started to masturbate me. My penis became erect, and when it did, he put it in his mouth. I was scared, but the feel of his tongue on the tip of my penis was fantastic. After a minute or two I climaxed. Not sure if it was a dry or wet climax, because he didn't take his mouth off my penis until it got soft.

    After that night I never said a word to anyone about what happened. I am married now, with two sons. I don't know if they will ask to be scouts, but if they do, I'm not sure I'll agree.

    1
    # 46079 - by Anonymous
    - Childhood Confessions -
    Straight Male / 35

    At 14 years old I was just short, skinny kid. My mother used to always remind me to stay away from the local railroad station restroom on my way from school. Of course, I didn't.

    One day I stopped there to take a piss, and as I went to leave, two older men came thru the door. The one man asked me why I was in such a hurry to leave while the other man pulled me into on of the stalls. I was too afraid to scream, and not strong enough to break free.

    The next thing I knew, the one man pulled my pants off and then my under shorts. At that point the one man remarked that I had a nice sized dick for such a small kid and started to fondle me. As I started to get hard, the one man dropped to his knees and took my dick in his mouth. After a minute or two I got completely hard and started to feel a tingling sensation in my dick. The men then traded places and the other man took me in his mouth.

    It wasn't long before I climaxed and squirted my cum into the mouth of the second man. The first man then started to fondle me again, and it wasn't long until I started to get hard again. Just then there was a noise outside, and the men both ran out of the restroom.

    I never told anyone about what happened, not even my wife.

    3
    # 46057 - by Anonymous
    • - Childhood Confessions -
    Straight Female / 30

    In my early teens my parents took an assignment overseas. That first summer my parents invited my boy cousin to come spend a few weeks with us, take him around to see the sights and expose him to life abroad. That was weekend stuff, during the week we were home and the most things we did was watch television.

    He was on the floor on his back and I walked up to him to ask him a question, I had on a skirt and he told me he could see my panties. I grabbed my skirt and walked backwards away from him but he crawled over to me and grabbed my leg and the next thing I know I was on my back and he was on top of me. He held me down with his chest while his hands worked my skirt up and he started to push my panties down. He then bit my tit, and when I reacted he pulled my panties off and I was on my back and he was looking square on at my pussy.

    The blood was rushing through me, he had his hands on my knees and I tried to keep them together but he won out and he opened my legs until I was splayed out and he stared at my pussy. His hands went down the inside of my thighs until he got to my pussy and he ran his hand over my pubes and then his finger up and down my slit. He held my thighs apart and leaned down and his tongue pushed into my pussy and he started licking, finding my vagina he started to push his tongue into me. After a few moments he got up on his knees and really ate me out.

    He stood on his knees starting at my pussy, he told me what it looked like and that he could see my hole. He undid his pants and his penis was erect. He leaned down on me and I put my arms around his neck and I felt his penis penetrate me and he fucked me slowly asking me if it felt good. He pulled out from time to time to eat me and then back on me to fuck me. He got on me one last time and he fucked me and he smiled at me while he came.

    After than afternoon on the living room rug we fucked on the bed, both of us naked. He liked opening my legs and looking at my pussy, I would lay with my legs wide apart and let him look. I liked it, I liked having my legs open and laying naked with him. I learned to get him hard by pulling on his penis and stroking him, sometimes sucking him. Once he was hard I waited for him to get on and fuck me.

    Those three weeks was the best sex I have ever had. I try to recreate it, but it just isn't there. The best I can do is lay naked on my bed and open my legs and use a toy and recreate the feeling in my mind. I have to accept that sex at thirteen and sex at thirty just isn't the same thing.

    0
    # 46056 - by Anonymous
    - Childhood Confessions -
    Gay Male / 53

    OK, just remembering the good old days. My first time came about when I was eleven and I would go spend the afternoon next door. The boy next door was fourteen and he had a large collection of comic books. I liked to read them laying on his bed, totally engrossed in them when he jumped on me and started to hump my ass. His dick got really hard as he humped me telling me that I really liked it. Well I did really like it, it felt good in a way that nothing had felt that good. His rhythm slowed down and he pressed hard into my butt, he had undone his pants and his naked cock was rubbing against my pants, he grabbed me hard and got me wet up the back of my shirt. When he pushed off he dug his nose into the crack of my ass.

    His dick was larger than mine and he made fun of me. He sucked my dick real hard and I had my first wet orgasm. He stopped sucking me and accused me of pissing in his mouth. He liked the cum and after licking it off his mouth he got back to sucking my dick.

    He liked my naked butt, and while I read comic books he would pull my pants down and rub his face over my butt cheeks and sometimes take my hips in his hand and blow air into my ass crack. After a while he started to stick his tongue into my ass crack and lick my butthole. It was that time that he put his dick up against my butthole and I felt his hard dick against me, it felt good and I asked him not to stop. He said I liked that and he tried to fuck me but couldn't get his dick in.

    The next day he used his mother's night cream and I got my first ass full and my first load. Getting fucked felt really good and I would take my pants down and lay on the bed and wait for him to get on my back and fuck me. I don't know if at that time I liked it better when his dick went in or when his dick was in, I loved having him on top of me and I loved his dick fucking me.

    By the time I was fourteen he was seventeen and in high school and he didn't hang out with me anymore. It took a long time for me to get over him, he ignored me. We never spoke of it, not to each other and not to anyone else. He went on to be a doctor and I am sure that he is queer, even if he did get married. He has that look, and I can't see how he isn't considering how much he liked to fuck me and suck my dick until he got my load in his mouth. That and that he liked to lick my ass. You don't outgrow that.

    A big heavy set man on my back with his dick in my ass still feels very good, I have a retired cop that fucks me and I suck his cock. He likes for me to make breakfast for him and serve him in bed and suck on his cock while he drinks his coffee.

    1
    # 46053 - by Anonymous
    • - Childhood Confessions -
    Straight Male / 34

    When I was fifteen I met another boy who had come to visit his aunt and stay with her for a week. He was my age and really nice and we sort of hit it off. I still don't know if he was really gay or not, but he was very persuasive. Somehow we started enjoying the fun of being romantic as boys, which was something that I had never done before and thought that I would probably never do.
    After just a couple of days of our being romantically playful, I let him butt fuck me. This was something which he had obviously done with other boys, and I never had. I still to this day don't know how I worked up the nerve to actually do that, but when we did it was so cool enjoying that with another boy. It was great feeling him being male with me like that, and having his stiff penis in my butt, and to have him ejaculate his sperm in me. That week I let him fuck me four times and it was absolutely the most amazing experience.
    After he left and went home, we wrote to each other for about a year. Then our corresdspondence fell off and of course I never saw him again. To this day I still think back on my brief love affair with another boy and I am glad that I had it.

    0
    # 46052 - by Anonymous
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