imconfused first not knowing you or your boyfriend i need to ask you would you use a strapon on your boyfriend if he asked and would you enjoy it? If yes don't wait to be asked speeking from experience its difficult to ask for, take the lead second i personally wouldn't recommend telling him that knowing he likes shemales wouldn't make you love him or think any less of him show him by trying what he wants also never tell him that if the relationship ended you wouldn't tell a soul or use it against him that may scare him by making him think its at the back of your mind. You seem to have a good idea of what he wants and if you like the idea instigate it if he see's your open to new things it make him feel relaxed enough to be more open with you us men are a strange breed;
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