Chest Pillow Cuddles
Guys have a very comfortable place to rest one's head between the shoulder and pectoral muscle. One of the most popular and comfortable ways to cuddle is for one person to rest her head on this spot.
Suggestions:
Wrap your arm around her while she is resting there.She is probably going to fall asleep. If you are not going to sleep, try to have a TV remote or something nearby so you can occupy yourself for a while without waking her. Prematurely spoiling the cuddle because you get bored is lame.Encourage her to come up a bit onto your torso, preferably with her arm draped over you for more support, like in the picture I shared. Try to keep the weight on the spot and not on your arm. If only her head is on your chest and none of her body, this can put a lot of stress on her neck, especially if you're a beefier guy. When she wakes up it will be sore and uncomfortable for hours. If she falls asleep with her neck in a bad position, try to pull her up or change to another position after 15 minutes. It should be relatively straight and normal looking.
Spooning
Probably the most popular style, spooning is when you cuddle front to back. The person in the back is the big spoon, the person in front is little spoon.
Suggestions:
It is common for little spoon's hair to get all up in big spoon's face. If you're little spoon and have long hair, try to push it under your head into the pillow to prevent nose tickles and other discomfort for your big spoon.The biggest problem with spooning is the arms on the underside of the bodies, the "trapped arms." If you have a couple grand sitting around burning your wallet, you can buy a cuddle mattress to address this problem.If you lack that money, I suggest the little spoon slide her bottom arm under her pillow. The big spoon has limited options, but one is to slide his trapped arm in the notch between little spoon's shoulder and head, under her neck. Little spoon should pull her pillow up tight against her shoulder to add extra padding between the arm and her neck. This will prevent neck pain as well as big spoon's arm from going numb. This position can be cuddled in all night if done correctly.Front Cuddles
Front cuddles are like spooning, except you cuddle face to face, as if hugging. It is ultimately an impractical cuddle position, as there is guaranteed to be at least one trapped arm holding more weight than it ought to.
Suggestions:
One person can slide their arm through the other person's neck notch, but doing so for both trapped arms is impossible. The best solution is to keep this a short-term cuddle position.An imperfect solution is to blend the chest pillow cuddle position with the front to front cuddle position by having the larger person rotate mostly onto his back and the smaller person moves mostly on top, as in the picture. Gravity works against this position in the long run, but it puts significantly less stress on the bottom arms.Interlock the legs.
General suggestions
Match your breathing as much as possible so you are not inhaling each others' breath.If you have a free hand and you're both awake, make use of it. Massage their back, rub your fingers through their hair, lightly claw.Have lots of pillows available to shove into any and all necessary places, whether that's under heads, between legs, or anywhere else. The norm will either be for the cuddles to stop as you readjust or for one or both cuddlers to wake with neck or back pain. Sufficient pillow distribution can prevent this dilemma.Keep the room you're in cool if possible, and the blankets light or medium weight. Cuddling tends to get warm and sweaty over time.Put a little sheet between your bodies if necessary to distribute heat and absorb sweat.
Relax and have fun.