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Sister-in-law always regretting not seeing my dick
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EDIT : "Stepsister" not "sister-in-law" damn… in french those words are the same, so I switched them up.

To start from the beginning, my father started dating the mother of two girls back when I was 11-12 year old. The eldest daughter was coincidently the same age. So we went through our puberty and horniness phase at the same time. Once puberty hit her she because a SMOKE SHOW. Tits big and perky, waist tiny as fuck and more importantly : a big fat round booty as giggly as can be.

We "played" a lot during our teen years : grabbing and slapping her ass, her sitting on my lap, hugging tight, etc. Being weird virgin teens, we never got to anything serious tough, but the tension was definitely there.

As we grew older and started getting into relationships, we came to talk a bit more about our partners and experiences. At one point she ended a 6ish month relationship and when I went to discuss it, the subject ended up on their sex life. After telling me how unfulfilled she was, she finally admitted that the guy had a small one. The conversation went something like this

Me: Oh.. do you know how big he is?

Her : not sure, but like.. 4 inches maybe?

Me : Oh yeah, that’s not that much to make you feel stuff..

At which point she paused for a second and looked me down a bit

Her: I don’t think it was that much about the size, but just how he did it.

Me: But that must not have helped haha. Have you been with someone bigger before?

Her: [One of her ex] was pretty big.. like maybe 6"

Me: Oh ok, well that’s not THAT big either

She let out a laugh and said something like "Oh ok, i guess [my gf] has sooo much more to enjoy eh?". To which i said in a confidence i never had "Maybe… and she loves it I tell you".

She was obviously getting awkward and looking back on it, very horny. But being a stupid 18yo thinking she was out-of-bounds, I went in my room.

Fast forward a year or two, she started dating another guy and during a family reunion, she went on a walk with my girlfriend and proceeded to tell her how HUUUGE that new guy was and how wonderful that was. The following is just what my gf told me, so maybe not 100% accurate.

Her: I’ve never been with someone that big before it’s crazy what it does to me!

Gf: Hahaha yeah the first few times are really mind blowing

Her: Wait, did you go out with guys other than OP before?

Gf: No, maybe you don’t want to know about your stepbrother, but he has some tools.

The conversation stopped there and a few months later, her mother and my father broke off in explosive fashion, resulting in me stop seeing her very abruptly.

I thought this was the end of it until a few years ago where she snapped me out of the blue very casually. We chatted for a bit and eventually got to our bodies and how we had changed. She snapped me a picture of her in normal but tight clothing. She had gained some weight and some of her crazy curves, but had still a solid booty and tits. I said I liked her outfit (she’s always been really into fashion) and she asked what I was wearing.

Me: Nothing special tbh, sweatpants vibe you know

Her: It’s fine, I wanna see you too

I went into full on fishing mode. Making sure I had a solid semi that showed through my pants, lifting a tiny bit my shirt to show the abs and flexing the rest. I wasn’t into working out back when she was in my life, but I now had some definition to my body.

Her: Damn, you really had a glow up! I’m kinda sad to not see that everyday now

I took my chance there

Me: Kinda sad I don’t get to touch that ass every day

She sent me a picture of her fat booty in a g-string with a "that ass?" caption.

Me: Damn, you’re making me hard, I never thought I’d be able to see that ass in my life

Her: I’ve been thinking how I never got to see all of you and it’s always been kindof a regret of mine.

Me: what do you wanna see?

Her: you know

I then snapped her a picture of it and she sent back the hottest picture i ever saw to this day. (I will forever regret not screenshoting it). Her huge tits were out and squeezed between her arms. Her tongue was in the frame and she drooled all over her tits.

The snap sequence went where you think, but I tried to organise to see her (I was now in an open relationship), but she denied because she was engaged to her bf (the same from earlier).. so the story sadly stops here (for now), but I thought it was worth sharing.

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3 months ago