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Im a 14 yo male and iv been masturbating for round 2 years, Iv been wanting to get into anal play but idk how to safely. Any tips / Guides for how i should start ?

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Do you have a big penis on hard?Try massaging your balls ,then move on to shoving things up your ass,like a Sharpie,can you cum yet?
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Do you have a tight ass ,try shoving a dildo up it ,it will take you 20 minutes to cum
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If you have not tried it before just try inserting one then two fingers up your ass,try to massage your balls at the same time,you should cum loads
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Try watching some gay porn,they will shove things up there ass using lube or vaseline,hope that helps

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Yes i can cum but is their any health concern or lube that I should use to prevent injuries

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No health concerns ,just shove up what you want ,do you have a tight ass
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