NEED ADVICE ON MY SISSY BOYFRIEND
from Vanessa

Dear Helga,

My name is Vanessa, and I am writing to you from one of my boyfriend's email accounts. I do not want to chance my children seeing this email. Anyway, I have been in a relationship for over 2 1/2 years with a man who I love very much. He slowly introduced me to bondage and also to his interest in feminization in the bedroom... and even a tiny bit outside the bedroom. For a long time I explored this with him, even adding on things like making him shave his armpits and keeping his other body hair very short. He also really likes me to wear pantyhose, lingerie, even lycra/ spandex too. I have indulged him in most everything. He also has begged for a chastity device, which I have told him would probably be okay, but I don't really have the desire to run out and take the initiative on that. He wants to get pierced and to have a "real device". I have tried to understand his desires, but I am having trouble. The best way he can explain it is that he enjoys the tactile feeling of hose and lycra, etc. and that the feminization part is like taking a "vacation from himself." It seems to be a very powerful aphrodisiac with him, and he points out that I have had great sexual experiences partaking in these games with him.

We used to have a lot of regular sex, although there was always at least pantyhose involved. I have had a lot of back problems and for a brief while he did too. Due to that, our sex life changed into more of a mutual masturbation session, and I took that opportunity to try to get fully onboard with the feminization thing. I would fully immobilize him in various different ways (he has a lot of bondage gear) while he was dressed completely like a girl... hose heels, bra, dress shoes, shapewear, whatever. (The funniest part is that he and I are about the same height, so almost all of my heels fit him. :-)

Then I would tape his mouth shut and do things like make him listen to feminization hypnosis recordings from the internet before eventually removing the tape and making him beg for sexual release by my hand and saying things to completely humiliate himself so that I did not stop. Let's just say that I humiliated him in just about every way possible. He seemed to thrive on it. For whatever reason we did not have vaginal intercourse for over 1 1/2 years. We seemed to both be happy doing what we were doing. He begged sometimes for regular sex, and when I would tell him "no, you can only get it like q girl" it turned him on even more. I thought that I wanted vaginal sex, but he points out that I must have been enjoying myself, as I kept putting it off or saying no. He has expressed a desire to sometimes take this lifestyle outside of the bedroom, like being my French maid for a day or something like that. We have never really acted on that though. He keeps telling me that finding a guy like him is like "hitting the jackpot" in some ways. I am not sure if I see it that way or not.

Due to some recent changes in my life I have started feeling a little uncomfortable with some of this stuff, and I have been telling him I want back off of it a little. I'm not sure why I feel this way, but he is disappointed. He says that it is hard to go backwards now. I guess my question to you is whether or not it is common for a woman to start feeling this way in this lifestyle? Am I feeling like I want more of a man? Should I be glad I have someone who is into this and so readily submits to me? Should I be glad that I have this kind of control? I get the whole thing about how I could make him completely obedient and sissified, but maybe you can help me understand why this is so great. I just wanted to hear from another woman. I could never bring this up to any of my friends or family, and he suggested that I contact you for advice. I would love to hear your opinion, and sorry the long email.

Sincerely,
Vanessa


Thank you for your letter Vanessa and for the background on your relationship and if I understand what you're saying is that he has in fact been rather selfish sexually speaking, you indulged his fantasies and basically did as he desired.

Circumstances in our lives change all the time, we adapt as they do, and yes, many people come to this lifestyle, try it for a time, then stop and do something else. Many women prefer to be in control, to have a submissive mate and there are many advantages, at least superficially, like housework, sex slave, etc. for many this is perfect and fulfills their life, others use the sissy for service and seek out real men as lovers. I can't suggest one way or another which is right for you, but fortunately you can try various things and see what you feel comfortable with.

Helga

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