- When I Was A Kid -

Straight Male / 55

Convincing Mom

I started fantasizing about ejaculating in from of my Mom at an early age. By the time I was 15, she had caught me masturbating several times. One day after catching me masturbating in the basement with a pair of her panties, she sat down with me and ask me if I was purposely masturbating in hopes she would catch me. After several minutes of denial, I finally told her my fantasy of masturbating in front of her. She seemed uncomfortable with the conversation at first, but then she nervously started asking questions about the details of my fantasy. She said it would be inappropriate but added she didn't think badly of me, but it should only be a fantasy. She told me I should only masturbate in private. She said It was ok to keep a pair of panties in my room. Then she ask me, in my fantasy, what was she doing? I told her I fantasized she had on sexy lingerie. I told her she would talk while I was masturbating . She ask what she would be saying? I said she would say things like " Your cock is so big". And, " Are you gonna cum for your Mom"? She was very serious when she ask me, " When it's time for you to ejaculated, what do you fantasy happening "? I told her I fantasized cumming on her " Where do you fantasized ejaculating on me"? I told her sometimes I cum on your stockings. Sometimes I fantasized about her spreading her legs and letting me cum on her panties. Sometimes she turns around and let's me cum on her big round butt. Sometimes she knelt in front of me and tells me to cum in her silky brunette hair. But my favorite fantasy is cumming on her beautiful face. She said of all those fantasy's, she would only consider one. She said she was going to think about this for a while, and we could talk about it later. She got up and started going upstairs. I ask her " Which one would you consider Mom"? She stopped, and without turning around, she said " I recently saw some very naughty lingerie that I have considered buying. Up until now, I've had no reason to buy it. I would consider wearing it for you, and letting you release into my hair". She then continued up the stairs. I jacked off the biggest load ever right then and there. More to follow.

That's Juicy! 63
Remove It! 9

# 77566 - by Mothers Little Helper / March 15, 2025

Comments

by Anonymous on Mar 15, 2025 at 2:48 PM

Later that week, my Mom ask me if I had any plans on Friday night. I told her the guys and I were going bowling. My buddy's Mom was going to drop us off, and pick us up. She asked what time I planned on getting home. My curfew was 9:30 on weekend nights. I said probably 9:30. She never looked at me as she was folding cloths. Well, I thought about your fantasy, and if we make this our secret, I think I could accommodate your wish. I stood in silent shock. "Are you serious Mom"? She look up at me, " I bought a very special outfit to wear, and if you promise not to tell a soul, we could have a little fun honey". I ran up and gave her a big hug. I then called my friend and told him I couldn't go Friday night. My buddy asked why, and I said " My Mom grounded me". I told my Mom I was staying home Friday night. She looked sternly at me and said " What time do you want me ready "? More to come.

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by Anonymous on Mar 16, 2025 at 1:02 AM

Continuing on. So then there I was. Late night in my mom's basement, typing this bullshit decades later in the hopes some stranger will know how deranged I am.

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by Anonymous on Mar 16, 2025 at 8:32 AM

C'mon man, Give it a rest already.

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by Anonymous on Mar 17, 2025 at 2:30 PM

That Friday night my Mom called me upstairs. I walked into her bedroom. She was in her white satin robe. She smiled and said "You really want to do this"? I said " More than anything Mom". She asked if I locked up downstairs. I had. She ask me to lock her bedroom door. She said " I don't want to take any chances on someone walking in on us". She got pretty serious and said " Remember Sweetie, you can never tell a soul about this". I quickly answered " I swear Mom, I will never, ever tell anyone ". She looked down at herself, " I'm going to put some finishing touches on. When I come back, I'd like for you to be on my bed, with a pair of my panties, playing with yourself ". She continued, " I'm going to act like I'm mad at you for doing what you're doing, just play along". I was rock hard. Mom left the room. I took off all my clothes, and jumped up on her bed. There on the pillow was a sliky pair of white panties. I'd masturbated several times with that very pair. Through the years, I've tried to find a porn model that resembles my Mom. I recently came across Kelly Monroe ( Pretend Model) .
She's on Instagram and Onlyfan. She is a full figured brunette who looks exactly like my Mom in the 80's. Back to my story. I could hear my Mom's high heels coming down the hard wood floors in the hall way. The door slowly opened. My my gasped " TYLER !!! WHAT ARE YOU DOING IN MY ROOM"!!! More to come.

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by Anonymous on Mar 19, 2025 at 8:26 AM

I wasn't acting when I yelled out " MOM !!!, I'M SORRY"!!! I instinctively covered myself. She walked to the side of the bed I was on. " Are these my panties "? As she snatched them from my hand. "I'm sorry Mom, they're just so silky ". She now was staring at my hard on. " You really shouldn't be in my bedroom doing this ". She sat on the bed next to me. " I should be very mad at you Tyler ". I started to touch myself again. " Do you like touching yourself in front of your own Mother "? I softly answered " Yes, Mom". She had such an intense look on her face. " Would you like to see what I have on under my robe Tyler "? I begged " Please Mom, please". She turned her head and spoke into the distance, " Well, I don't know how I feel about this young man. Do you want Mommy's pretty panties back"? I nodded yes. " If I give them back, I want you to wear them for Mommy". I answered " Mom, I'll do anything you want, but I like to rub them across my balls. They feel so silky across my balls Mom". She stood up and untied the belt on her robe. " I have something even silkier to rub on your balls Sweety". More to come.

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by Anonymous on Mar 19, 2025 at 10:44 AM

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by Anonymous on Mar 19, 2025 at 8:03 PM

Sorry for the double post. My Mom opened her robe, slowly pulled it down past her shoulders, then let it drop to the floor. She stood in front of me wearing a white corset with garters. She had on baby blue sheer stockings, and matching baby blue see thru panties. Her white heels must have been 5 inches tall. My Mom was 5' 7" tall. In those heels she seemed like a giant. When she turned around, I found out her panties were actually a thong. Her gorgeous big ass jiggled as she turned in her heels. The front of her corset barely covered her 38DD breast's. Her corset was so low, I could see the top of her areola's and some of her nipple. She had on more makeup than usual, and her hair looked incredible. I don't think I had ever seen her hair look so soft and bouncy. Her hair was just past her shoulders, and she smelled amazing. She leaned in close to me and whispered in my ear, " Would you like to cum in Mommy's pretty hair little boy"? I whispered up to her " Yes, Mommy". She smiled and kissed my ear. She got on her knees right in front of me. She spread my legs, and moved her body close to my hard on. She looked me straight in the eye and said " Do you cum alot honey"? I told her I masturbate quit often. She smiled and said " I meant when you final cum, is it alot of cum"? I told her I didn't know if it was or not. She said " I hope it's enough to soak my hair, but I have some other ideas to get my hair dripping wet". She turned around with her head right in front of my crotch. " Pull the front of your panties down under your cock and balls". I did as she said. She tilted her head back so her silky brunette hair fell down on my cock and balls. Her hair was silky, and cool against my balls. " Now, grab my hair and wrap it around your cock honey ". I did exactly as she instructed. I was masturbating with my Mother's beautiful silky hair. It wasn't going to take long for me, but I tried to make it last. Then she said " I'm such a naughty Mom for letting you do this". I kept thanking her, and tell her I loved her. I told her " I'll do anything for you Mom". She knew I was getting close. She said " I want you to stand over me and cum in my hair sweetheart ". She lowered her head and I started rubbing harder against the top of her head. She started getting louder " That's it baby, cum in Mommy's hair Tyler, do it baby, soak Mommy's hair with your cum. GIVE ME YOUR CUM TYLER, GIVE ME YOUR CUM"!!! I exploded. I shot seven large streams of cum repeatedly in my Mom's hair. As I moaned with each climax, my Mom was screaming, "YES, YES TYLER, CUM FOR MOMMY, OH GOD TYLER, CUM FOR YOUR MOMMY"!!! It was the greatest sexual moment I have ever experienced. I was in a sexual trance. My Mom's hair was soaked with my cum. She immediately was touching her hair. She said " Oh god baby, you did sooo good". I had no idea what else my Mom had in store for me that night. More to cum.

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by Anonymous on Mar 20, 2025 at 2:55 PM

Very hot indeed! Looking forward to the rest!

by Anonymous on Mar 22, 2025 at 6:13 AM

My Mom also seemed sexually wired. She was so excited. She seemed addicted. And she clearly wasn't done with our play time. She turned around to face me . She continued to play with her hair as she said " Do you need a little time before you can cum again"? I excitedly said " It doesn't take much time at all." She smiled " I have something I want you to do while we wait". She got up and walked to her night stand. She picked up a glass of water that had been sitting there. She walked back and knelt in front of me. " This is warm water, I want you to take a big sip, and swish it around in your mouth for a while. I want you to get the water full of your saliva. After a good few minutes in your mouth, I want you to spit it all out into my hair". I was instantly hard again. " But Mom, it's gonna get all over you". Her smile leftbher face, " That's the whole idea honey, I want you to soak my hair, my face, my entire body with your cum, and saliva water. I want to be your naughty cum slut ". More to cum.

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by athensgold124 on Mar 22, 2025 at 12:44 PM

Nothing like a mother's love.

by Anonymous on Mar 22, 2025 at 8:55 PM

I took a big sip of the warm water. I kept it my mouth for a couple minutes. I could tell a lot of my saliva mixed with the water. My Mom sat on the floor in front of me as I sat on the edge of the bed. She had put a couple of towels under her on the wood floor. She looked up eagerly at me. " Are you ready to drench me Tyler "? I nodded yes. She then closed her eyes and said " Let all that saliva water pour out of your mouth, all over my hair, and face. I leaned over and put my hands on her shoulders. I pooched my lips, and slowly let the thick water pour from my mouth all over the top of her head. She then turned her face up, and I continued to let the saliva water cover her face. She opened her mouth to catch the thick liquid. She then spit out her saliva and mine, all over her chin and down her neck. Her hair and face were dripping wet. Her tits were glistening with the saliva water. She opened her eyes, reached down, and pulled the front of her corset down, exposing her soaked titties. Her nipples were huge and hard and sticking out a inch long. She pulled her right tittie up to her mouth and started spitting on her nipples. She took turns with each breast spitting and licking and suckling. Her black eye liner was running. My Mother looked like such a slut. " Are you ready to cum again Tyler "? I could hardly talk, but I managed to whisper " Yes, Mom". I was stroked my cock, when she spit on my cock. Her saliva poured from her beautiful mouth. I instantly started cumming again. This time she directed me to " Cum on Mommy's titties honey". I unloaded all over her huge titties, saying " I'll do anything for you Mom, I'll do anything you tell me to do Mom". She never smiled, she just looked at me and said " You will obey everything I tell you tonight Tyler. And if you do that for me tonight, the next time we have our little date night, it will be my turn to obey you". With that she started licking her cum soaked nipples. She looked at me and said " Take another sip of warm water, I want you to let that beautiful saliva water pour on another part of Mommy's body". More to cum.

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by Anonymous on Mar 29, 2025 at 6:28 AM

I could barely speak. " Mom, I'll do anything for you ". Without a smile, she looked up at me," I know you will do exactly as I say honey". She stood up, and grabbed my face with her hand. " Did you like cumming in front of your Mommy, Tyler "? I loved the feeling it gave me when I told her, " Mom, I love being naked infront of you.I love touching my dick in front of you. But most of all, I love cumming on you while you watch". She gave me a naughty grin, " Do you think you could cum for Mommy one more time sweetie "? I nodded yes. She let go of my face, and grabbed the glass of warm water. " Take a sip, and hold it while I tell you what Mommy wants." I took a big sip. " Mommy's going to get on the bed on my hands and knees so my big butt is in position for you. I want you let all that saliva water pour out over my butt. I want you to rub it all over Mommy's butt. Then I want you to spank my big, round, wet ass. While you're punishing Mommy, I'm going to play with my pussy. I want us to cum together baby. Does that sound good to you Tyler."? I nodded yes. She got up on the bed. Her ass was already wet from all the saliva water I spit on her head and tits. Her baby blue thong hardly covered anything. The string had pulled to the side exposing her tight butt hole and her shaved pussy. She looked back over her shoulder at me. "If you feel like pulling my hair when you spank me, you can. Mommy knows she's been naughty, and I deserve to be punished ". She kept her eyes glued to mine. She reach down and started fingering herself. " Let it pour out on Mommys ass baby ". I obeyed my Mommy. Her ass was now soaked. I reached up and grabbed the back of her hair, pulling her head back firmly. She gasped with pleasure. I watched her fingers going in and out of her pussy. She would also move her fingers to her butt hole. When she touched her beautiful butt hole, I smacked her ass. This became our routine. She fingered her pussy, then she knew if she touched her butt hole, I would slap her butt. I played with my dick, pulled her hair, slapped her ass. She was moaning and saying, " Mommy's such a slut. Punish Mommy, Tyler. Spank Mommy hard, Tyler. Spank me until we cum together baby". We finally both reached our climax. She buckled over and screamed as she came. " OH GOD YES, YES, YEEEEEEES". I shot my cum all over her butt, up her back, and into her wet hair. We both collapsed onto her bed. She was breathing hard. I was motionless. She turned to look at me. She smiled. " This is our secert ". I smiled " Of course it is Mom". Still smiling, she brushed the hair from my forehead. " Bet you never realize your Mom was so freaky did you". I smiled and said, Can we do more stuff like this Mom"? She leaned over and French kissed me on the mouth, then smiled and said " Next time, you're the one in charge youg man". More story's to come.

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by Anonymous on Aug 18, 2025 at 5:32 AM

Giggity!
Very well written and hot!

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