Familiarizing Yourself with a Bra
Find a bra you can use for practice. Volunteer to do the laundry. Make sure no one is around, and then take a look at your mom's or sister's bra. It might seem weird at first, but it can take a while to learn to unhook a bra with both hands, and this is an easy way to get some practice. You can buy a bra cheap at a thrift store--just pretend you are shopping for your girlfriend or for a costume party. You can order something online that is like a fabric bracelet that clasps around your wrist using the exact eyelet and hooks you would find on a bra. You can use this to practice unhooking the bracelet with your free hand. If you're a girl then it's a little easier and you can practice with your own bra.
Check out the mechanism that keeps a bra fastened. Most bras have two wide straps (or bands) that connect across the back. A series of hooks are stitched to the end of the left strap (assuming the person wearing the bra is facing you), and eyelets sewn on the right strap. (If the person has their back to you, then the hooks will be on the right and the eyelets on the left.) There may be one hook and one eyelet, or somewhere between 2 and 5 rows and columns of hooks and eyelets. Some front-fastening bras have one large hook that slides down into a loop of fabric, rather than side to side or forward and back, like with the hook and eyelet.
Practice unhooking the bra with one hand. You can fasten the bra around a pillow or rolled up sleeping bag--something roughly the size of a human torso. This will pull the bra strap taut so you can practice when there is tension in the strap. You may want to start by just hooking and unhooking the bra when it is loose and there is no tension in the strap so you can get the feel for how the eyelets hook and unhook. Practice using first one hand, then the other, to see which one feels better. It may not necessarily be your dominant hand.
Unhooking a Back-Fastening Bra
Slide your hand up the back of her shirt to her bra band. Run your hand over the center of her back and feel for a slightly bulkier section of the bra made up of thicker fabric, or the gap where the hook and eyelet are connected. If the back of the bra is completely smooth, she may be wearing a front-fastening bra, or a bralet or sports bra that has to be removed over her head, like a shirt. Now would be a good time to confirm that she wants you to proceed. When your hand is on the clasp, simply pause and ask her, "Is this okay?" Don't disrespect your partner by assuming she's okay with you taking off her bra. If she says no, stop what you're doing and go back to making out. Make sure your hand is warm before you slide it under her shirt. It could be an unpleasant shock to place a cold hand on her warm skin.
Slip your middle and index fingers under the band and pull it away from her body. Your two fingers should be right underneath where the band fastens, or under eyelets where they meet the hook. This should relieve some of the tension that keeps the hook securely in the eyelet.
Place your thumb on the other side of the band. Pinch the fabric between your thumb and your two fingers. The section of fabric you are squeezing should be where the two sides of the band overlap. If you are only grasping one layer of fabric, nothing will happen when you try to unhook the bra.
Slide or push your thumb over your two fingers, unhooking the hooks. Make sure you are pinching the fabric tightly. It is almost the same movement as if you were snapping your fingers, only using three fingers instead of two. You may also want to think of the movement as squeezing or pinching the material between your fingers and thumb while sliding your thumb forward so the hooks release.
Unhooking a Front-Fastening Bra
Move you hand up between her breasts and feel for the clasp in the center of the bra. It will be made of metal or plastic and should lay flat against her sternum. Most women wear bras that fasten in the back, so check her back before you try to unclasp the front of her bra. Though it's probably obvious what you're doing, make sure she's okay with what you are about to do. It doesn't have to be a big deal and can even be kind of sexy. Just pause and whisper "Is this okay?" If she tells you yes then you can proceed. If she says no, don't try to force anything. Just remove your hand and enjoy kissing her.
Slide your middle and index finger under the clasp and lift it away from her body. This relieves some of the tension in the bra. If it is not an eyelet closure, there may just be two metal or plastic pieces that snap together and lock when flat against her chest. If this appears to be the case, spread your fingers so they are on either side of the clasp.
Press your thumb against the clasp. If the bra is fastened with a hook and eyelet, then you will make the same snapping, squeezing movement as you would with a back-fastening bra. If not, you will need to push one side of the clasp up so that it unfastens from the other side. Pinch one side of the clasp between your thumb and index finger and pull up while your middle finger pulls down on the opposite side of the clasp. The hook is not always on the same side, so if this doesn't work, try pressing your thumb against your middle finger and pulling up while your index finger pulls down.
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