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Here’s my situation and I want to know if any of you ladies can relate.
My best friend knows about Vanessa. He’s never met me as her in person but he’s seen pictures. He always tells me how good I look and he’s proud of me for expressing myself to him. I’m lucky that he’s dabbled in drag and CD in the past, he is a few years older than me, so I’m very comfortable with him.
But lately I’ve been fantasizing and even dreaming of him being sexual with me as a woman. I like the idea of it because I’m so comfortable with him, but I’ve never told him about it. I don’t want him to actually have sex with me, but he’s my only chance of a man treating me like a woman.
I would love to be treated like a woman with an actual man, and he seems like the best shot I have at it. I just don’t know how to approach him.
I really want to know what you ladies think. Have any of you been in this position?
Me personally I havent. 😊 my wife and I are best friends so its more about us enjoying each others company.
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I have spoken with several girls here and elsewhere that eventually want “the whole girl experience” with a man. Listen to the advice and take this carefully! You need to make sure your either gay or bi, or that being a tg woman is what you are. There will be unintended consequences for taking that path. Be careful and really think this one out. Don’t loose a supportive friend for a romp in the hay. He may not want to do this or expect it to become a real relationship. Good luck.
🍷C
I would agree with Carolyne, do not loose a supportive friend just for a ‘romp in the hay’. If you really are attracted to men you will find the right person, sometime, but try not to be in a rush. When coming to terms with who we are, all sorts of emotions come to the fore, not all will remain with you for ever, so before you take that leap consider very carefully any consequences that may arise.
Take careA few years ago a dear friend of mine, who also happened to be my roommate, “discovered” me one night when he wasn’t supposed to be there. I was a mess, but he became very understanding and assured me he would keep my secret. He encouraged me to be and embrace Helena, which to me was almost to good to be true. I did, but not too much as I didn’t want to overdo it. I saw how he would look at me and how he would talk to me as Helena, and it was…flattering. In time, I went back to dressing when he wasn’t there just because I enjoyed myself better alone. It was when he started to all of a sudden tell me he had feelings for me, that I got scared and decided that I needed to be alone. I could not reciprocate because I did not feel the same. It was a year ago come this August that I moved out, and got my own place. He would often call or come over trying to get something going, and at one point I felt I owed it to him since he was the keeper of my secret and well, I wanted to see how it would feel like. Big mistake. The night he came over, I was in Helena mode and we talked over drinks. He sat close to me, complimenting me, complimenting my outfit. Patting my leg he moved in to kiss me. I let him, but in that instant, I could not do it. I valued him too much as a friend and I did not want our friendship to be affected. Typical of a guy, he got upset. Very upset. He got up to leave and told me not to call him or contact him. I was scared to death that he would reveal my secret, but it is now 9 months and though I have not seen him since, he has not revealed anything.
I do miss him though, very much. His name is Greg. He was a true friend, easy to confide in and a true gentleman. I hated myself after what happened because I felt it was my fault. He saw the real me, got to know the real me, and was in love with me and I just pushed him away. Who does that? But I realized that I was wise to keep boundaries, because I valued our friendship more than wanting to be lovers. Does that make sense?
There are days I want to call him and tell him I’d like to give us a try, but I think he has moved on. And I think I only want to because it sucks being alone, and he is someone who doesn’t judge me and hopefully maybe still loves me. I’m so conflicted. But the thing is, is that he’s kept my secret safe. And…I love Greg so much for that.
I have fantasized romantically and sexually about Greg numerous times and wonder if it would have worked out. I know that he would have been very good to me, treating me as I would like to be treated as a lady. I’m left only with that. So, Vanessa, I would advise that if you feel it truly in your heart to take it a step further, that you have that conversation with him and see where it leads. He already knows Vanessa, and that is a huge plus. That’s the main hurdle. I hope that if you do, it goes so well for you. You deserve that happiness.
I appreciate everyone’s stories and words of caution. I think I was in a lonely mood when I posted that and wanted to express myself.
I do want to clarify. I didn’t mean specifically intercourse, to be entirely honest. I’m 100% faithful to my wife and he to his. He and I are both bisexual, though and we’ve made out as guys. He is someone I would feel comfortable with, regardless of how I look.
That said, I don’t know how he would react and treat me as Vanessa. I hate the idea of losing him as a friend over this, but knowing him, I doubt that would happen.
Thank you again for all your kind words.
A quick update to this post: my friend finally met me as Vanessa. All he could do was stare at me, tell me how beautiful I was and we made out a bit. Nothing more than that. It was kinda how I expected and he left in a hurry. I’m honestly glad someone else I know personally met me. It’s more relieving than anything
He left in a hurry or had to go? Sometimes when men are attracted to us they start to question themselves sexually. So I wouldn’t be surprised if he felt a little weird about it afterwards. It’s perfectly normal especially when one has a religious background. Start to question morals and ethics. Sounds like you like him or who he is as a person. I wonder if he ever called back or did he distant himself. I know this is an old thread but curious.
P
Vanessa, my first step with a male was with a friend I discovered was gay before he ever knew about Gina. I had been crossdressing for some time and really wanted to take Gina to a new level, to see if I really wanted to go through life as a “woman”. I also contemplated where our relationship might go but one night I met him and surprised him as Gina, as prettied up I could manage to be. That led to my first intimate encounter with him and a relationship that lasted for several months until he left for the military. It was an enlightening experience for me and I enjoyed every bit of it. However, that was the only relationship I had with a friend who also knew me in my male persona. Since then, I have had several relationships with men, both good and bad. I would recommend being open and honest with yourself first to determine what you really want to experience before taking the leap.
Vanessa, I, Can tell you a quick story I have been dressing for a number of years and some friends know. I hadn’t told anyone that I didn’t trust. However I got on line and started talking to him and well any way we became lovers and we saw each other once a week. I, was bi
and after therapy sessions realized I was gay. Now, the man I met was a gentleman and one night I invited Him over and I felt the overwhelming feeling That I wanted to kiss him and we had a very long make out session and we had sex. This continue for a long time then he hadn’t called ao heard from him an then out of the blue he emailed me if he could come over and I said sure and well any way an I wanted his kisses and wanted him. He just made me feel like a real women. How ever he did his thing again and and hadn’t heard from him for a long time. I, finally heard from him and told him I think he was just using me for a sex stop only ! Well I haven’t heard from him in Months now and I do miss him and his kisses and hugs. and I think I love him. But I can’t do the yoyo seeing and not seeing him so I gave up on him. Its just to emotional So I tell you to take your time and be careful !
Hugs,
StaceyOmg how fun!!!! I might mention to him that you have had thoughts of being with a man who treats you like a lady. Then shut up and let him reply. Ask him maybe if he ever had those thoughts when he dressed fem.
btw i can tell you that doing so will bring you to a level of femininty you never knew existed.
Hi , All That was a great story and very heart warming. At one point in my life I thought about the same way and since a teenager I had some dealings with other males as Grew and started Dressing at an early age as we all did I started have the same feelings and cted on them very slowly and met someone on line in my area. We Met and talked the first time and chated on line and the invite to my home for some coffee and chatt and the feelings over came me that I wanted to go further and we landed up in a heavy makeout session and which turned out to go further and no further explanation here. We had several more sessions after that.
He was always a gentlemen and respected me told me How good I looked etc. I don’t see him as much these days as has moved and I still think of him and fantasize About him and me together.
This was and still is the best experience I have had with a man. Good Luck to all.
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