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Helping my sister pop her cherry

625 words | 4 |4.31

My sister wants to be ready for her boyfriend and asked big brother for help

So today my fellow degenerates, I bring you a story that happened just now. And I don’t regret it. I woke up at about 10:40 am today, ( it’s 12:30 as of finishing this story, and we ended at 12:00) an my sister (15) came in asking me (17) if we were going to do what we planned today. For context, yesterday I gave my sister a bullet vibrator that came with a fleshlight I bought last week. She told me she didn’t know how to use it, so I showed her a few ways. I showed her the usual vibrator to the clit, inside her pussy, and while getting more creative I told her I’d need to touch her to show her a few more ways.
She decided to let me so I put a finger inside her and had the vibrator between my finger and her clit. I also put the vibrator inside while holding it and rested a finger on her clit, while thrusting the vibrator in. She really enjoyed it and I left her to it.

My sister is about 5′ 9″ and has a small frame, with small but perky tits and a decent ass that has some damn good jiggle. I’m 6 feet tall and im a lean build with broad shoulders and a decent amount of muscle. I’m not the most attractive but I’m good enough to be popular with girls if I tried ( I’ve done it before, not my favorite time in high school)

That same night, my sister said she struggled with getting more than a finger in at a time so I explained that because she was a virgin she hasn’t stretched out her hymen and it would hurt until she did something about it. She explained to me that she was failing to because it hurt to much to do, and asked if I could help. Of course, I gladly accepted!

Back to this morning, she came in and asked me if we were going to do it, I drowsy as hell didn’t understand until I remembered last night. So I got up and patted to my side, telling her to sit down.
I got up and grabbed lube from my bathroom and slipped on a condom (as per her request) and lubed her up. We spent the next hour just slowly easing my dick in her and stretching her EXTREMELY Tight pussy, and fitting it around my 7 inch dick. Afterwards we stretched her out in the cowgirl, reverse cowgirl, and doggy style poses.(we were in missionary until then)
After a few breaks between and the time at 11:40 she told me that the condom was adding to much friction and it was hurting, so I asked if she wanted to stop or take it off. Much to my glee, she said take it off.
After being back in missionary for a while she said she needed to stop. I asked her if I could finish before, and she happily agreed.

So I spent the next 20 or so minutes slowly thrusting in and out of her wet hot cunt, feeling every little ripple and bump. Ironically, we stretched her in a way that she hurts less the deeper I am. So I’m gently fucking her and stretching her out and I feel her contract around me, she covered her face and let out little whimpers. I asked her if she came, she only nodded, I picked up my pace and made full thrusts. I wish I could’ve enjoyed her more but I pulled out as I climaxed, the streaks of hot cum reaching to the underside of her perky little tits. After she got up, she went to take a shower, and she told me “let’s finish stretching me out another time!”

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4 Comments

  • Reply TARA ID:49kap65h5qr

    I can’t remember who popped my cherry ! Either it was my stepdad or brother or granddad !!

    • Datboi ID:fx7o5ntzk

      Id like to think it was your brother!

  • Reply [email protected] ID:2qlj3enm3

    Email or session me Op would love to know more about your sister.
    05111798fad96b7a10a3c7adf1aa09f6831bbba9b44f7182d042b0566e976e5121

  • Reply Kevin ID:1eldpk4xop1v

    i love young bro sis stories