How do I pack my kinky stuff for going through customs and airport secuirty? Will Jamaican customs search me and stop me from coming in or take my toys?

You have to go through customs both entering Jamaica and returning to the US, Canada, the UK and likely every other country. In our experience, it is highly unlikely that you will be searched going into the Jamaica as a tourist going to a resort. In the past it was also highly unlikely that you would be searched coming back from Jamaica as a US citizen ( I can't speak for Canada or the UK, but I assume it is similar). We are only aware of two people being searched in Jamaican customs going to events in the last 8 years, and each time they had an unusually large amount of luggage. 

Going into Jamaica, if they were to search you, they generally won't ask or care about kinky toys, sex toys, or rope as they are looking for commercial merchandise that they can tax or illegal items like weapons. We are told that the customs people saw whips, nipple clamps, vibrators & wands, rope, hoods, and canes, and were told they were "toys". The customs officers did not care about those items, confiscate them, or subject the attendee to additional questioning. Coming into the US they are looking for contraband such as drugs or illegal items. Again, they likely won't care about kinky toys either. 

If you were to be asked about rope or kink toys, you will have to use your own judgment as to how to respond, but we prefer to tell the truth because lying is a crime and telling the truth likely won't be an issue.  We can say this: Hedonism has been around for a long time (since the 70's), and customs has seen it all including hundreds of people going to other kinky events at the resort. This will not be the first time that customs in Mo'Bay has seen kinky items. If you are going to Hedo and they find kinky items, they likely won't care and won't really be surprised. As long as it does not appear to be commercial merchandise, weapons, or illegal items, you will likely be good to go. 

On the other hand, there is a list of prohibited items that we recommend you leave behind. Of note on that list are handcuffs, knives, swords, "riot gear", pepper spray, cross bows and long bows, firearm accessories and ammo, and camouflage clothing.

It is also important to note that handcuffs are technically illegal in Jamaica. Again though, if you say it is a toy, it may not be an issue. 

It seems that anything that could be a weapon or used by the military is likely going to be subject to scrutiny in the unlikely event that you are searched. That said, we don't recommend that you bring extreme items like tasers, cattle prods, or  swords or knives, etc. Use your best judgement and keep items to a personal supply.

Also, we suggest that you put most if not all of your kinky stuff in your checked bag. We have heard of TSA / Airport security conducting searches of carry on bags with items like ropes and whips. That may be okay, but stuff in your carry on is scrutinized more than stuff in your checked bags. and of course, make sure you don't have your cutting tools in your carry on. Again, use your best judgment!