First: the best way to stretch a virgin hole is to start with a virgin who believes his hole can be stretched. If he’s not totally into it, it’s no fun for anyone. If you really want to get fisted start by becoming friends with your dildos. Once you’re comfortable enjoying your own hole find an experienced versatile fister, preferably one with medium or small hands to play with. It will take several sessions, but keep practicing. With one exception I’ve never opened someone for the first time on the first date. By going slow you’ll build trust in your top, and he’ll know your hole well enough to know when to push. He’ll also know when to pull back. In all your play let your top know what’s going on for you, both what’s working and what’s not. Fist fucking is not a contest.
If taking a fist is your sole objective on a date you’ll frustrate yourself. Absorb the energy of men you play with and what turns them on. Get comfortable with their touch, their smell and their attitude. Paying attention to how other bottoms respond is also a great way to learn how to enjoy a fist. If you are certain you want to take a fist let it happen when it happens. Be kind to your butt. It’s your friend not a bad boy that needs discipline. Also, be kind to the man topping you. Your mind has to trust both him and your body before it lets your muscles relax. That takes time and includes not just how well you know a top at a party or bar but something about the rest of his life like his friends or his history growing up. You want to become friends because then the ride is always more fun for both of you.
Advice to tops: If you’re playing with a virgin be sweet. Start with massage and kissing to relax him. Make the whole thing fun. The last thing a Newbee needs is someone telling him what to do because he’ll immediately feel inadequate if you do. There are no rules and no single way of fisting; it’s mostly chemistry. Chemistry develops through small talk, even pictures from your last trip or stories of strange relatives. Laugh at your silly mistakes. Make the bottom feel very special and not just another piece of weekend meat. You are playing with not just a man’s hole; you’re playing with his self confidence. You’re also probably playing with eighteen things you’ll never know about him.
Each of us sees ourselves as a sexual being differently, and no one fits a mold, so each of us comes to fisting with a unique profile. It’s important to honor that in a virgin. Once he’s comfortable with you, let him tell you what he wants either verbally or through his body language. Trust me; his body knows what it wants.
Never force it. We call fisting “ffun” because it’s all about having fun. Begin opening the bottom by teasing his butt muscles. Then with a steady hand allow him to slowly swallow your fist. If you’ve never fisted anyone, don’t even think about it with a virgin! All of the incredible tops I’ve had the pleasure of having inside me also know how to take a fist. Partners and husbands on the other hand can do whatever your relationship permits; if you trust each other you can both have fun exploring as giver and receiver.
In the end: Fisting is no sport for amateurs. Stretching a virgin hole requires a genuinely interested bottom and an experienced versatile top.
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