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Preparing to Tickle Your Boyfriend
Determine if it's the right time and place. Sometimes it can be tricky to know if tickling will be viewed as cute and playful or annoying and inappropriate. Consider your location (if you are in public, he might not appreciate giggling madly in front of a bunch of people), and his current mood. If you've just been fighting or he's angry, now might not be a good time to poke and prod him. Listen to what he's saying. If he's confiding in you that he's heartbroken over his dog's death, he probably needs a hug more than he needs tickle torture. Wait until you're somewhere relatively private and have room to wrestle a little and not injure yourselves. Make sure he's not holding a hot beverage or something that might injure him or you when you catch him by surprise. Don't try to tickle him when he's playing video games or absorbed in something that is really important to him (even if you are annoyed that he's not paying attention to you). This is when tickling is just annoying, not fun. If you two are joking around and he's in a good mood, he probably won't mind a little tickle.
Figure out if he's ticklish. Your tickle attack will fail if it turns out your boyfriend isn't even ticklish. Do a little exploring first to figure out where he's most ticklish. The most vulnerable spots on the body are also the most ticklish Poke him in his side, just above his hip or in his ribs and see if he giggles. Give him a hug and "accidentally" tickle his armpit. This is one of the more ticklish spots on most people. If he's laying down with his shoes off, gently run your toes along the bottom of his feet and notice his reaction. Kiss him gently on the neck and exhale through your nose so the air hits his ear. See if he gets goosebumps on his neck.
Make sure your nails aren't too sharp. Sharp nails might be good for tickling if you plan to just graze them over his skin (like on the underside of his feet or the back of his neck). But if you plan to really get into a tickle war, sharp nails may become painful.
Tickling Your Boyfriend
Sit next to your boyfriend on the couch, bed, or ground. Smile and get close to him, maybe cuddling or kissing him a little so he doesn't suspect anything.
Slide your fingers under his arms and wiggle your fingers in his armpits. Move your fingers like you are typing rapidly or as though you are gently scratching a dog behind its ears. The key is to use a fairly light touch--if you use too much pressure tickling can quickly become unpleasant and even painful. Try and get him to stretch his arms above his head so he is fully exposed for an attack. Stretch first and he may instinctively copy you. Or say something like, "who wants ice cream?!" and raise your hand. He'll probably do the same (unless he hates ice cream). If he's laying down you can straddle him so he can't escape and he's more vulnerable.
Run your fingers up and down his sides. Think of your hands as little crawling, scurrying spiders. He will probably try to stop you by pressing his arms against his sides. People will automatically try to defend themselves by limiting your access to vulnerable areas.
Tickle the bottom of his feet while he's busy defending his upper body. His feet will be vulnerable, so grab one foot in one hand and use the other hand to tickle his foot. Be careful that you don't get kicked. He may begin to jerk his legs away from you and kick you in his struggle to escape.
Finish by sweetly nuzzling his neck and alternating between giving him little kisses and blowing on the skin. This will tickle him, too, but it's a nice way to show him that this was all in fun.
Don't tickle for too long and stop if it seems like he's really not enjoying himself. Some people really hate being tickled and, even though they are laughing, it will make them really angry. If he tells you he's not in the mood, starts yelling, or starts thrashing and kicking, you should stop. Don't tickle him for more than 15-20 seconds. If he says he's laughing so hard he's going to pee in his pants, believe him and stop tickling.
Be prepared for retaliation. It's unlikely your tickling will go unanswered, so if you are dishing it out, you better be ready to take it. When you stop tickling your boyfriend, pull your arms tightly against your body so he can't access your armpits. Tickling can be a very flirtatious action, and it's likely that, during or after the struggle, someone will initiate making out or fooling around.
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