Ok, so this is all new to me. My on again/off again of 5 years (henceforth referred to as TGT) first shared his cuckolding fantasy with me 3 years ago (whilst he was engaged to someone else). We have been 'on again' for a couple of months now and in that time I've taken cuckolding off the table as it doesn't float my boat (at the moment). He then introduced chastity and showed me his (poorly fitting) cage. Which intrigued me. So a month ago we had our first play with chastity and oh my god! THATS what's been missing from my sex life for all these years! Then, my estranged mother was found dead and I had a fairly impressive emotional wobble and he stropped off. I do actually love this man - have done for years - and as of this evening, he has said that he wants exclusive, casual, friends with benefits with me. Which I'm fine with, we live 25 miles apart, we both have jobs that take us away, but I trust this man implicitly (I have literally put my life in his hands in the past). Where in the name of all that is holy do I start?? I've read loads of websites, I'm discovering my Domme side, but how do I actually get started? He's sub and looking for humiliation but gets frustrated and tops from the bottom. I'm not going to see him for a couple of weeks whilst sorting out the funeral etc (the other end of the country from me) and I want to blow his socks off next time we're together. I have the basics down (we have epic sex, we both agree that this is the best sex either of us have ever had) - but how in the name of all that's holy do I control a sub who has been fantasising about this for years, give him what he wants and still be able to work out what I want/need? And yes, I get that we probably ought to be in a more stable relationship, but I leave the country at the end of the year and we have agreed this is the best chance we will both have to work through and find out what floats our individual boats before we're over for good. Call it my entry-level FLR
You get it but have no idea of how an unstable relationship can turn into no relationship very fast. It will not work out because you need to be dominating from a place of love and be around daily, not just every few weeks. Eventually he will want you to dominate him the way he wants to be dominated and not in a way that you will enjoy. Your on and off again relationship can be dangerous as you may end up dominating him from a place of anger at times. It sounds like he is done with you, but like any other guy, will not refuse free sex with no strings attached. If you are thinking that dominating him will bring you two closer, I would think again. For it to work, especially cuckolding, you need to have a very stable relationship. I was a cuckold in an unstable relationship and it ended in about 10 months and not under good terms. It takes a long time to learn to be a good domme and an on and off again long distance relationship does not present the best situation to make it work. If you ask him for help, he will have you doing what he likes and that makes him the dom, not you. I have trained a few women to be dominant but it took a lot of time together and a lot of experimentation. What is good for one man may not be good for another. You need a very intimate relationship to make what you have in mind work. Most stuff on the internet is pure fantasy. Professional dommes do have all the equipment you see but they are playing a role that someone pays them to pla. Do you think a guy will turn over a few hundred dollars to have things he does not like or want, done to him? Anyway, you will do what you want. I have been a sexual submissive for 47 years who trained three lovers to dominate me. One was my Mistress for 30 years. She did not get really good at it until a few years had passed and many more years to be great at it. That was in a very close live together relationship.
I agree with @Vinny ! Given that it will all be over at the end of the year, why not just sit him down, have a sincere, heart to heart about what each of you desire between now and the end of the year, don't kid yourself or him and then simply act out a plan that will fulfill what both of your want/need between now and 12/31? You could have some pretty hot times in that context and won't leave anything undone!
Well I for one think it's a grand idea for you both to be able to explore each other's fantasies before heading out of each other's lives. It sounds like you both already have a handle on your expectations relationship wise and really just want to enjoy the remaining time together. And to be honest I didn't see a question on your post asking if if anyone thought it was a good idea or if it would work or if should attempt. It sounds like you will be doing this and wanted to know how to be the domme he's been fantasizing about, and still explore your desires gradually. If you already have an idea of the activities that turn him on, it's all about the timeframe you are comfortable doing them. I would say to be very in control and verbal, even about activities you aren't doing yet. Example... he wants you to peg him...you tell him "I will fuck you in my own time or perhaps never, if I wanted an opinion from a small dicked chastity slave...I'd ask you for one." That kind of talk gives the sub something, the firm control and humiliation he craves, and still gives you the time you need to do the activities you want at your pace. I'm sure you'll do great, good luck.