Just discovered this sub and thought I’d share one of my first sexual encounters. When I was young, I travelled a lot due to my dad’s work so we’d often spent time away and would often stay at friends places when we’d go and visit. They’d almost be like extended family in a way and we are all very close.
It was the start of lots of my kinks… the receiving instructions, the cuming on clothes, clothed sex, seeing women masturbate or thinking of women potentially masturbating have become massive massive turn ons so if this does, I’d love to hear about it (as a comment or in my inbox)
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My parents friend, back then, was in her early 40’s typical cougar kind. She would always love ‘hanging’ over my shoulder to look what I was up to, not hesitating to push her breasts up against me or you know gently rubbing my back whenever we went there. At 18, I had had a girlfriend or two and no longer a virgin, which she knew about and well at 18 you got the hormones rushing.
She had facebook and had several bathing suit style pictures on there that I loved jerking off to especially when we’d go and have a sleep over there. I’d jerk to them in the bathroom or in bed at night and man did my fantasies run wild… dreaming about just slipping the bathing suite to the side and driving him in, or sliding it under that tight bikini top and just go to town on what I think were 32DD’s. I generally jerked into a towel as well. One, I loved the feeling and two, it meant no cleaning and that towel started to have an ever so slight discolouration in a few spots that she must have picked up on. So here I am again and her place, beating my meat, thinking everyone is in bed when she walks in the room. I freak out a little and hide under the blanket. “Sssshs it is fine, show me” she said. She stood there in her jeans and tank top that had my mind running wild the entire afternoon as they only barely contained her tits and her ass, in those jeans, just looked amazing.
“But you are my parents friend, I shouldn’t” I remember saying and her reply is what won me over. “Well, you got me on your screen, you have been jerking off to me for a while how is this any different? You started this so you better finish it”
Those last words just had him twitching under the blanket and she knew it. “Let me join you” she said and before I new it she had her jeans unbuttoned and a hand sliding down into it. The sight of that hand going in panties has marked me forever. I get ultra turned on these days whenever I just see a woman playing with herself. The idea of a woman slipping her hands down her clothes, panties to touch herself and tease herself… just gets me rock hard. As she stood there I could see her reaching her clit as you moaned slightly, that did it for me, I started rubbing while watching her playing and teasing herself. Her body pulsating at her touch, my hand following her rhythm as I stroked him from balls to tip. Slow and then fast, slow and then fast. “Show him to me” she said. Still a little hesitant I looked at her, straight in the eyes, she nodded yes, her eyes fixed on me “Please” she said as another little moan escaped her lips. I pulled the blanket away and there he was, still wrapped in that towel. She laughed. “I knew it” she said “You know how often I have rubbed my pussy on that towel knowing it contained your seed?”. Today I am convinced this is where my love for dirty talk started. Hearing that was such a turn on that I just wanked him faster and faster. Barely in control as an 18year old, horny on hormones would. “Slow it down a little, let me enjoy this moment, slowly reveal him to me” I slowly unwrap the towel and low and behold my cock, standing tall, standing firm. The head wet from precum as I had been jerking and edging even before she came in. Her hands speeding up in her panties and her nipples pointing straight through that white top. Hearing her moan I cant resist but stroke my rod at the pace of her hands rubbing her clit. She pulls her hand out, “Look how wet you made her” her fingers glistering, she walks in a bit closer to show me. “Here, use some to lube him up” without asking any permission she wipes her fingers along the side of my shaft. Needless to say he was twitching and pulsating at her touch. She laughed a little and plunged her fingers straight back into her panties, curl them this time so she could slide them inside her self. The space needed pulled the jeans tightening around her bum showing off that amazing figure. Her other hand had slipped under her top and was caressing her breasts. My eyes were fixated on them, something I regret a little as I love seeing a woman sliding fingers into herself but the way she was cupping and grabbing those breasts… eugh… it had me pumping like a piston in an engine.
Her hips and legs started rolling as she was standing there, fingering her pussy while staring at me stroking my cock. She sees me staring at her tits and walks in closer and places a hand on the fabric of her white top. Her boobs feel soft underneath the shirt, heavy as well, held up by a black lace bra I had managed to distinguish during the day. “Fondle them” I eagerly oblige and squeeze in them, rub them and have the palm of my hand slide over her nipples. she moans and breaths louder as my hand touches that one nipple. Excited by the sound I let go of my cock and just do the same with her other nipple. Both hands teasing her… my passion for teasing and pleasing woman was born. As my playing with her nipples had her fingers sliding and pumping her pussy even faster.
“You are an evil little man” she says. she pushes me back and raises her top a little. “Payback” is all she said and before i knew it my cock disappeared under her shirt, the warmth, the softness, the tightness, thanks to that push up bra, overwhelmed me. I couldn’t see where my cock was but it felt like it slipped past the bottom of her boobs and now making its way in between them. She started moving up and down on them, my cock eagerly pulsating between them. She felt him pressing up against her chest each time she went down. Every time she came up I saw her fingers still inside her panties, rubbing, teasing. She pulled her top down a little exposing more cleavage and the next time she came down on him the tip of my cock appeared between the top of her tits. I could have almost blasted my load right then and there but the fact she didn’t come right back up made me just ooze a little precum. With her free hand she rubbed it between her chest and came right back up. “careful, he is going to cum if you keep going like that” I stammer, my breathing louder and louder but barely noticeable as she is grinding herself up against the bed. Her body starting to shake and move a bit more uncontrollably as I say it. Her hips grinding against her hand. The pleasure she was taking in playing with her self. “Don’t hold back as I won’t, cum all over me” she said… wait what? did I hear that right? was she going to keep stroking my cock with those massive 32DD until I popped a load all over them? my hips start pushing up from the bed as she starts coming down on them. The thought of just fucking her tits while she is about to cum herself… my entire body was into this now. slamming up against her chest, my head sticking through the top of her tits more and more almost hitting her chin. She is smiling, moaning as she looks into my eyes: “good boy, keep pumping those tits, they want it, I want it” as she says that her body starts to spasm, shake. I can see her palm pressing down hard on her clit as the fingers are buried deep inside of her. No longer moving I can see her under body push against her hand as she lets out a moan.Her neck and chest red, her breathing stopped, her eyes closed all the while i keep slamming in between her tits. As she opens her eyes she licks her lips, swallows and catches her breath and smiles at me. That smile is with me today and something I want all of my partners to have when we have sex. That look of ultimate satisfaction. It is what did it for me as she pushes her breasts together, sliding up and down my shaft I stiffen my body, my cock sticking out straight, the veins pulsating. Up and down, up and down and as she comes down, her beautiful tits fully wrapping themselves around my cock, cum starts squirting out, it hits the bottom of her chin and the force at which its shoots out has it bounce back and run down her tits, onto her top, the amount of cum flowing out after almost an hour over edging before overflows, the head of my cock soaked, her tits soaked, and like a volcano keeps erupting more cum keeps flowing out. thick strands of cum running down her shirt and dripping onto my body. She smiles as she keeps stroking him gently with her boobs as I try and catch my breath. Little spasms still as her tits touch the tip of my cock. “Hand me that towel, would you” as she gets back up. A wet spot clearly visible on her panties and jeans, her chest and shirt covered in cum my cock soaked from my own. She wipes it off her chest but leaves it on her shirt and smiles. “I’ll keep this as a souvenir” she says “Have a good night” as she makes her way to the door.
Source: reddit.com/r/gonewildstories/comments/bq3qzt/how_that_one_time_getting_caught_shaped_my_sexual
This story turned me on!
Sure hope you did more with her.
Any more stories with her?