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@confessions
24 May 2023 9:56PM
• 2,896 views • 1 attachment
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When I was 22, I was still living at my dad's place when he started seeing someone seriously enough for her to move in with us. He literally dropped it on me last minute, but it was still his house I was living in and I didn't care as long as he was happy. Only problem was we were living in a 2 bedroom 2 bathroom duplex, and his new woman was bringing her then 19yo daughter with her. I do remember being mad at first, because we were going to be sharing a bedroom AND bathroom. Any anger I had drifted away once we met. She was slim and petite, only about 5'4", but somehow was rocking the most beautiful C-cups you could imagine.

Now, I was certainly sexually attracted to her, but also a realist. The whole stepbro/stepsis thing is all the rage in porn these days, but that kind of stuff doesn't happen in real life, I thought. She was flirty with me from the beginning, but I always laughed it off cause I didn't want to get the wrong idea and then forever be the creepy stepbrother. They were only living with us for like a week before she would be in our room with me alone and in nothing but a towel or her bra and panties, after taking a shower. I was lucky enough to have had different relations with different ladies by this time in my life, but she really had me blushing and acting shy just because I wasn't 100% sure how to react.

One night, she had a pretty attractive friend staying the night and we were drinking a little bit, so the conversation turns sexual, as you do. I should be ashamed, but I lied to them about how sexually experienced I was so her friend starts daring her to flash me and before I know it, they are both topless telling me to show them how I'd rub a girls tits. I was a boobs guy 100% then and her friend was that girl who had double D's since 6th grade, so I'm just sitting there, one handful of the friends boob and the other handful of my stepsisters boob, going, "Is this good? Should I pinch the nipples?" xD

So I'm instantly rock hard and trying to hide it, but they want me to show it to them. And I'm telling them no because dicks aren't pretty like pussies are. So they get to whispering back and forth and giggling and then my stepsister says that if I show them, her friend will give me a handjob. I'm still feeling like a shy virgin at this point because of their forwardness, but I pull it out and they giggle and whisper more until the friend gets up and tells me to come into the bathroom with her. She's still topless with just her shorts on and she doesn't waste any time once we get in the bathroom. She gets down on her knees and starts jerking my cock. We were only in there for like half a minute before there is a quick tap on the door while it immediately opens up and in comes my stepsister, who is also still topless, and in a sexy little voice she says, "I wanna watchhhhh."

I'm not saying no since my pants are already off and dick out, so my stepsister sits down on the toilet while I'm standing there RIGHT in front of her getting jerked off by her friend. At this point, I'm grabbing and rubbing on both of their tits, and they are talking about how wet their pussies are and it's just getting hotter and hotter. I hadn't been sexually active at that time for about 3 or 4 months so I had already been close to the edge since the start of that night. As soon as my stepsister came in and sat down, I said out loud, "I am going to cum so fucking hard." My stepsister hadn't touched me up until this point, but she starts playing with my balls right after I said how hard I was going to cum, and let me tell you, this was one of those orgasms that build and build and build until I was literally trembling up until I came. It was the most cum I'd ever seen come out of me, ever. I covered both her tits and it was just pouring down off her nipples, down her stomach, onto her shorts and all over the floor. They both kept saying, "omg. omg. omg."

All I remember saying is, "I have never came that hard." over and over again. I was still in the post nut daze, but my stepsister grabs my hand and shoves it down her shorts saying, "Feel how wet I am!" and she is indeed soaking wet. I get kicked out of the bathroom after this while they shower together and "girl talk". At this point, my shyness had faded and I'm wanting to get in the shower with them, but no dice xD. We had been alone in the house the whole time, but my stepsisters mom was off work a little after all of this happened, so we are all in the living room watching movies later that night and I'm just trying to act like I didn't just get jerked off by my stepsister and her friend haha.

Anyway, post is already too long, and it probably reads like I made it all up lol. I have a bunch more similar experiences that I might write up and post here too. Just wanted to share because even good friends I had at the time didn't believe me until I showed them the video proof haha. (Attached pic is my stepsister standing in the same bathroom they jacked me off in.)

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@confessions
02 Aug 2025 6:41PM
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Need some advice.

Ive been cheating on my wife for a while now. My buddy knows a bit of that. His younger stepsister was hanging out with us one day. She and I got to talking about relationships. She went on to say, "I know this doesnt sound good, but the reason I not looking for a relationship is I dont think theres anything thats gonna stop me from cheating." I acknowledged what she said but didnt divulge me situation. The conversation passed since her stepbro, my buddy, came into the convo.

I wanna talk to her more about it and see where it goes. I dont have her number but we've partied a couple times before when my buddy would invite her. Im not sure how to go about trying to have an affair with her and dont even know how to sus it out to see if shes into it.

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