new bi cross dresser here

[kstair9]

Hi all,
I'm new here. I've been playing around with some "light" cross dressing for several years now. I've made some interesting observations that I'd like to share, each of which can probably by psychoanalyzed to reveal something, but that is beyond my ability. I only like to dress when I am horny and I only like to dress slutty (thong, high heels, stockings etc). As soon as I do, my fantasies become, as many others on this board, towards being a woman with a man. I usually pull out a dildo and anally ride it. It doesn't even feel that physically good, but it makes feel naughty and I love it. As soon as I cum, I feel the same guilty feelings many of us do, and instantly no longer want to dress.

It gets even weirder. The latest thing I did is to film myself riding the dildo in stockings, high heels and a wig. I filmed it from behind so (even if I do say so myself) it really looks like a woman doing it. I really enjoyed doing that, my favorite part being when I'd swing my hair back from falling over face and make it land over back. For some reason that really made me feel like a genuine sexy woman. Anyway, that video is now my favorite video for me to masterbate to while a man. That is, I enjoy watching from the man's perspective, which is what I consider the most weird part. The hair swinging is also the best part to watch. Yes I know, weird.

I love sucking on the dildo as well and have had several bi experiences in real life, none of which I enjoyed. I've played with people I met online as well as a good friend who is gay. I hated every experience and finally decided maybe I am not bi despite my fantasies while cross dressed. It could be that I'd only enjoy being with a man if I were dressed as woman, but I'm not sure. The only time I ever enjoyed a real cock was during my one and only experience with a transexual. That experience was incredible. She was beautiful and I loved sucking on her cock.

I've discussed with my SO a little about cross dressing and she does not like it. She has a hard time accepting that I might enjoy receiving anal play too, so I keep all of that to a minimum with her. She's the type who is not homophobic at all, but wants her man to be a man. She likes to be the submissive one in bed. It may not even be that big of an issue because I noticed that I don't have the urge to do any of this with her. When I am with her I enjoy playing the man's role. I enjoy it a lot, even after I cum I want more. I see it as primary, whereas the cross dressing and bi-fantasies are secondary (although they have been with me for a long time now) and don't usually involve her. Since I am committed to her, I don't mess around on her of course, but I don't really tell her the extent to which I play with dildos when I am on my own. She's unaware I dress too. My only urge to tell her everything is so I don't have to hide it anymore, not so much because I want to share it with her because I am not sure I want to.
Although, I have to confess that if I were 100% sure she'd be able to switch from seeing me as a masculine man to a slutty woman and back to a man as fast as I do, I'd jump at the opportunity to have her dress me up and pound my ass. Although I'm not sure she could do that. If she can't do that, I don't think I want to sacrifice what we have for that experience.

Anyways, those are my thoughts that I wanted get off my chest. Any thoughts or comments are welcome.

 

[satinmarabana]

Hi kstair9, thank you for being brave and sharing your experience with us. I'm a woman who has had relationships with sissies (men who like dressing up as slutty women and being with me as I encourage them and use a strapon). Your story sounds very, very familiar. I've had it described to me in similar terms... not gay but fantasize about cock while playing a woman, etc. I don't have a lot of hopeful things to say regarding your SO, unfortunately. I don't think women change on something this basic. If she was experimental in bed or wasn't always traditional submissive, then it would be just a different thing to try, but it sounds like she's bought into the traditional roles and doesn't want to fulfill your fantasies. From what I've heard, even if she tries, it will be an unpleasant scene as she will resent having to do it and that will come through clearly in the sex play. The case I know about, trying it once damaged their marriage a lot.

Again, I'm sorry I don't have better news, but I'm living proof that women who like sissies are out here. If you're committed to her, commit to enjoying your sissy fantasies on your own. Sex is just a sliver of your life so if you love her, don't sacrifice that for fantasies.

xxoo
Satin

 

[kstair9]

Hi Satin,
Thanks for your input. I think you are right. If I really wanted to she would indulge me, but it would be an unpleasant scene. she wouldn't enjoy it and it may scar our sex life. She is experimental and I wouldn't call her "traditional" submissive, though. Maybe I mischaracterized her. We are less adventurous these days, but a few years back we used to role play, she used volunteer her ass for my cock, and the like. I still tie her up once in a while and she still loves lesbian porn. But she is not into me pretending to be a woman at all.

My main doubt is whether I should tell her the extent to which I play on my own. I don't need to play a woman around her, but it'd be nice not to always hide it. I don't think she'd take it well, so for now I am not telling her.

 

[johnie ringo]

Can only give you insight from my point of view and hope it helps. I have been married for over 15 years, with my wife for over twenty total. In those years I had many a fantasie that I would think about, read about, etc. while i pleasured myself. I always hoped my wife would participate in many of my dreams; however, I never knew how to open up the subjects with her, for fear of rejection. Now, I am not into dressing up like a woman,(not against it) but I always since I can remember have craved two fantasies more than any other, one was eating my own cum and two was having my ass fucked by a strap on.
Fast forward to about three years ago. I would say our sex life was pretty damn good; but as before, my two fantasies were never mentioned. I would drop what I thought were little hints, like rubbing my dripping pre cum on her tits and then licking them off, or playing with her ass in the hopes that she would return the favor. HAve always had an open relationship, but was too put off by thinking she would think I was "gay" or less of a man if I let her in on my little fantisies.
One day she found my litrotica web sight and asked me what that was about. Told her I liked reading some of the stories and maybe she should check it out and let me know. From there, I sent her a story, was basically a man and woman straight sex story, except it ended with him cumming on her tits and him licking it off!! I figured if she did not like it she would mention how gross the ending was or something to that effect! Well, when I got home she told me how hot that story was and especially the ending!! Hello, jack pot!
It was not long after that I was sending her stories about strap ons, as luck would have it, two weeks later, she was the proud owner of one.

There have been many discussions about the feelings and feeling comfortable about what is happening, but you can go to our thread "what a great strap on delight" and see how far we have progressed over the past few years. It was baby steps, one taboo at a time, keeping in a comfort zone. I agree with satin, sex is only a part of a relationship, an important part, but just a part all the same. If my wife never came down this trip with me, then I guess I would coninue logging onto the computer when no one was at home, reading and jerking off...not the worst of situations there either ...

 

[bluesky496]

Hi kstair9, thank you for being brave and sharing your experience with us. I'm a woman who has had relationships with sissies (men who like dressing up as slutty women and being with me as I encourage them and use a strapon). Your story sounds very, very familiar. I've had it described to me in similar terms... not gay but fantasize about cock while playing a woman, etc. I don't have a lot of hopeful things to say regarding your SO, unfortunately. I don't think women change on something this basic. If she was experimental in bed or wasn't always traditional submissive, then it would be just a different thing to try, but it sounds like she's bought into the traditional roles and doesn't want to fulfill your fantasies. From what I've heard, even if she tries, it will be an unpleasant scene as she will resent having to do it and that will come through clearly in the sex play. The case I know about, trying it once damaged their marriage a lot.

Again, I'm sorry I don't have better news, but I'm living proof that women who like sissies are out here. If you're committed to her, commit to enjoying your sissy fantasies on your own. Sex is just a sliver of your life so if you love her, don't sacrifice that for fantasies.

xxoo
Satin

sound advice satin ,i totally agree with your diagnosis.

 

[naughtyinsilk]

kstair9, I think you are stuck in an awkward situation, and I do sympathise, I think you will have to in the end discuss it further with your SO.

Although she may not wish to join you in your fantasy play, you need to come to an understanding that you will be doing it when she is not around. If she finds out you are doing it behind her back, that may damage your relationship badly.

In the end for both of you to be happy, there will have to be a compromise found that you can both accept. Carrying on as you are sooner or later, it will cause a wreck.

Good luck I hope in the end it works out

NIS