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Overall, the main aspect of the plug is the constant reminder of his submissive role. Feel free to couple a plug with his chastity cage.

Playful teasing actually gives him pleasure through attention. Another interesting and confusing thing to grasp.

This adds to the humiliation component and will give him comfort that you are alright with how submissive he is. If he is staying alone in the hotel room, you need to set the rules.

The knock on the door will be humiliating. Him having to throw on a robe over his sexy lingerie and answer the door is even more enjoyably humiliating for him.

If you really want to be devious, you can call the hotel room service hours in advance to request a bottle of wine be delivered to his room, but specifically request that you want the bottle to be room temperature and not chilled, even if the Zinfandel or Rose is supposed to be cold.

That way you can demand he shimmies down the hall in the robe to get a necessary bucket of ice. If you are with him in the hotel, the possibilities can expand.

Actually bringing others into the equation is up to you and discussed below. It could be fun having a third party or it could be a disaster.

Your relationship is built on trust with each other and not the third party. That might not mean all third parties would be unwelcome.

Maybe it would turn one or both of you on being watched by a third person on webcam? Once these things are discussed, these limits can be used to set the ground BDSM rules.

They can always be changed if you want to reduce the interactions with third parties or expand the adventurous boundaries a bit.

It might be of interest to someone on commission! I also mentioned the room service orders, but maybe it would be fun if someone stopped by the hotel room while your sissy was tied up.

So many possibilities that you and your partner could explore together. If you think three is a crowd, that is also fine too. Tasks can be used as a tool to get him closer to being unlocked, played with, or even orgasm, as you desire.

Buying panties, picking up dinner, massaging feet, etc. As an example, on Wednesdays, your sissy might be responsible for bringing home dinner, dressing in lingerie, giving you a massage, and serving you a drink.

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