First off, I guess that I should admit that I am a bisexual crossdresser, and was totally honest with my girfriend about the situation up front. She was Accepting of both, even to the point of buying me clothes and going out all dressed up together.
Although I was bisexual, I did not have relationships on the side, but she was aware of the past ones I Had had, I guess this sort of made it easy for me to introduce her to the idea of a threesome. We had many fantasies that we would think of while having sex, and mine seemed to always involve another man.
We had been together for 8 years before I finally made my move. I asked her if I could invite another guy over one evening, for me to play with. I told her that she was more than welcome to stay and watch, and made it clear that if she wanted to join in that it would be ok.
She is totally straight, but is ok with my other side. When she agreed to let me invite someone over, I was so happy and felt even closer to her. We both understood that love was not what I was seeking, but rather the experience of living out some of the fantasies we had been sharing. For her to allow me this, made me love her even more.
I took a few weeks to find just the right guy, and he just so happened to be a crossdresser as well. He and I talked quite a bit before the big night, and even met a few times. It was clear that we both eventually wanted my gf to join in.
He was quite surprised that I could allow someone to touch my gf in that way. I explained just how truly thankful I was for her to let me live out my fantasies, and how I felt it only fair to allow her to experience hers as well. And because she had no interest in being with another woman, and was excited by being with a man, it was the only reasonable option. Of course she was very conservative and did not express a true desire in going through with it, even though she was allowing me to do so.
I guess it was the many talks we had and the understanding that we we were simply exploring something new, and if it didn't work out, we wouldn't have to do it any more. It was made very clear to all, that limits must be respected, and falling into love was not an option. We were very much in love, and felt comfortable enough to know that nothing and no one could ever come between us. I suggested that our new friend be nothing more than a boy toy for us to play with as we saw fit. Of course we took his fantasies into consideration as well, and were willling to help him live out his as well. And most of those by the way, involved my gf. I told him that he had my permission to do whatever he wanted to do with her, as long as she agrees. Bottom line, it would be up to him to see how comfortable he could make her.
It took a couple visits before she finally joined in. I really wasn't sure how I would take it the first time, but it ended up being the most exciting thing we had ever had. Although she initally was a bit nervous, it wasn't long before I don't even think she knew if I was in the room or not when she was with him. She was obviously was enjoying herself, which made me happy for her, I even left them alone on numerous occasions so that she could relax a bit more. I wish I could go into greater detail about the various scenarios we got involved in, because they were all experiences I will never ever forget.
As our visits continued, sometimes it was just he and I, he and her, or all of us together. Whatever we did, it was the most exciting time we had ever had. He always checked with me first on things he wanted to do with her, and eventually, I just told him that he had my permission to do whatever the two of them agreed to, and that he should talk to her about things he wanted to do, I was always positive towards my gf and told her to just have fun with him... to have all the fun she wanted to. Let me tell you, it was intense, I even allowed them to meet at other locations by themselves. It was as if she was living out the fantasy of having an affair, yet it was always ok with me.
By allowing them, to be alone, I guess it allowed her to feel totally relaxed without worrying about what I was thinking. My only request was for her to have the time of her life. She also, by the way, allowed he and I to meet each other at various locations as well too. And when I came home, she would always kid me a bit about what we had done. Not knowing what may occur after us getting involved with him, I must say it was the most exciting time of our lives and brought us even closer together.
For it to work, you must go into it with the right mindset, and realizae what the purpose of it all is. As long as all 3 of us maintained a murtual respect towards each other, feel free to have fun! And we did... oh boy did we ever!