Rough Riders

To claim this quest:

While The Cowgirl has two holes to choose from, when she mounts up her saddle piece, some of her riders have only a single choice. With plenty of lubrication, and some practice, any longterm rider can handle the saddle piece anally. If you or your partner takes any attachment of a riding machine anally, and experiences orgasm on the machine (with or without extra assistance) you can claim the Rough Riders achievement.