This happened in the 90s. Since when I was 13 I had a really good relationship with Ellie, we both were school friends. Her parents would be out for 2 days so she invited me to sleep at her house, we were used to go to each other house when our parents were out and masturbate together, but we never had sex. We were watching porn when she told me I should try anal masturbation, I seriously thought that was a ridiculous idea, she kept telling me it felt good but I thought it was gay. She waited until I got distracted and got a finger inside me, It accualy felt good. She started playing with my ass and worked her way up to getting a cucumber inside me, when i started cumming she started licking my penis, that sensation was amazing, while doing a blow job she started getting the cucumber deeper and deeper and kept doing it faster. I felt that cucumber inside me for at least 2 hours, then she tried using a baseball bat, amazing feeling but I started having a little pain. She kept using it for over 1 hour and then she got a vodka bottle. Took her more then 20 minutes to get it inside, she played with the bottle for 30 minutes, then she got half of it inside me. She got her pussy on my penis and we had fun until i cummed. Ellie changed my life, I could never think something going inside me could give me so much pleasure, I do anal masturbation at least once per day since that happened
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