A good friend and I DP'd my boyfriend once and it was great for all of us. But we were all very relaxed and comfortable with each other, and we were careful about pleasure not pressure. Took it very slow, and we each fucked him a little first to loosen up. The position we used was both the tops on our backs heads opposite and legs scissoring, so our dicks were together. Paul sat down on them, nice and slow, then bounced his way to his own hands free orgasm. The feeling of the underside of my dick against our friend's was also amazing.

Find your own comfort level, tho. No tearing, please.

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