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My ex's sister
As a teenager i was curious about anal sex, my first girlfriend wasn't interested in it, one day we had no condoms so she said we could try anal (She was positive she would never give me a blowjob), i mounted her and put my cock against her asshole but having little knowledge i didn't know about lubrication and tried to just push my way inside, the head slid in but because of the pain she shook me off and everytime i asked after she wouldn't let me try again. A few months later we broke up, but kept seeing each other. Shortly after i got talking to her younger sister, she was worried her boyfriend would leave her if she didn't know how to give a good blowjob as she had never given one, she asked if she could practice on me, a couple of days later, she came to my house got on her knees and i pulled out my cock, she sucked it like a natural, she had said she didn't want to swallow, but when i was ready to cum i "forgot" to let her know and came in her mouth, after that this happened a few more times. One day during these sessions i tried my luck, now i knew what i was doing i lubed up and got behind her, and before she knew it my cock was sliding up her arse, initially she didn't like it, but after a few deep thrusts she moaned and begged me to fuck her harder until i came in her arse. For the next 3 years we'd meet up and i'd fuck her in her arse regularly. P.S During this time my ex not only gave me a blowjob, she swallowed every drop of cum.
I first bottomed for an older guy when I was eleven. I would occasionally be with older guys, discreetly, all the way through junior high.
My step-son is thirteen and we've gone off a few times and he has bottomed for me. I was not his first, his first happened with an older guy when he was ten and at a summer camp.
We take turns bottoming for each other and have been occasionally doing some sucking before anal sex. It's been a total of six separate times in the past four and a half months.
So far we've not taken any unnecessary risks to be together and he has been so exemplary in discretion. His mom hates anal but he makes up for it.
Once and only once, My chubby ten year old girl cousin allowed me to do anal sex to her when I was almost sixteen. It took me like thirty seconds of jumping to finish inside of her and pull out. It was embarrassingly brief but it was so erotic.