Should I give in to fantasy and be trained by a dom daddy?

[yngbiguy305]

***Deleted***

*****

 

[Miles Long]

I'm hoping to get advice, opinions and comments from those with more experience than I. I hope I'm posting in the proper section. Also a long post, but want to lay out a clear, initial picture.

In public I am a masculine, straight male, have a gf, dress conservatively and would be considered a "normal guy" in my late 20's. I have geat sex with my gf and am very attracted to women. However, secretly, in private for the last few years I have been crossdressing more and more and consider myself a submissive sissy. Also, a sissy who mostly wants to submit to masculine dom men. I get really turned on when I'm dressed, imagining submitting, dressed in sexy lingerie, to a dom man and pleasing him as his sissy boy. I've built up quite a collection of clothing/lingerie/shoes, a couple wigs, a little make up and a few toys I like to play with as well. They have all been well hidden. I have no desire to make any of this public to friends/family, nor do I wish to become a full time woman, crossdresser, drag queen, or tv. Furthermore, because of my career, it would be very very bad to have any of it made public. But, almost everyday, I find myself frequenting sites online that are all about sissy boys being dominated, looking up sexy lingerie I'd like to purchase and other new toys/shoes/accessories to help my look, reading blogs about it, etc...That alone gets me excited.

I have "played" with a few men while dressed up that I've met via the internet/CL, to varying degrees of enjoyment and fun. A few times have been some of the most intense sexual experiences I've ever had. I also met up with a part-time crossdresser/drag queen who encouraged me to go further, saying I could be passable if I really tried. No encounter has progressed beyond a hook up 2-3x and then lose contact (partially because of me, partially because of them.) But each time I think I'm sure it's really not what I'm looking for, it all come's back and I find myself dressed up, browsing online and fantasizing or thinking of finding someone to play with again. Even once I'm done masturbating, and I feel like my mind is clear of everything, even the slightest trigger (like a panty commercial on tv, or sexy heels, seeing a short skirt) will get my mind racing again, thinking about how great it would be to wear any of those items while being submissive.

When I'm dressed I feel really sexy, slutty and more turned on than I've been any other way. Just looking at my collection gets me excited and I wish I could wear it all at once, but I try to choose the sexiest combinations I can. I typically tuck my penis into tight panties, as I don't just want to masturbate and be done. I then can also rub myself like a woman and get just enough pleasure to feel good, but unable to cum. I love playing with my ass and feeling a dildo slide in and out and I love to suck on some of my dildos. It drives me crazy. Even after I've orgasamed, if I stay dressed, I will quickly be horny again, it feels almost perpetual. If I don't let myself orgasm for a while my thoughts really go crazy.

I recently started living in an apartment by myself, with no roommates and the gf in a different state, so I've been dressing a lot more frequently than previously possible. Recently, during a "session", I posted a personal add on a sissy site I've been on for a little while and received a very well written response from an experienced dominant daddy type. I replied back saying I was interested, but wanted to know more, etc... He replied back with more information and said if I was still interested, he would send along the first set of rules and we'd go from there....

This is where I am now and I'm not sure what I should do. On the one hand, being formally trained to be a sissy boy is my ultimate fantasy, especially when it is by someone specifically into this type of thing (opposed to hook up with a gay guy who tolerates a boy in lingerie, etc...). Also, I've already "broken the ice" with being with men. But, beyond the safety and well-being issues (which I fully consider and take seriously), I am hesitant about taking this next step and making it real.

Thoughts?...

Do it.

 

[subwannabe]

It will always stick in your craw until you try it. One thing though, you are going to have to decide soon what path you want to go down. Finding and keeping a gf who will be ok with your desires is going to be close to impossible.

 

[SweetErika]

Let your gf go, then do whatever floats your boat. It doesn't sound like this is a passing thing, so you at least need to do the ethical, responsible thing by breaking up with your gf before you go any further ( unless you believe she'd understand and support you, or at least not out you to anyone ). She has not consented to your sexual activities with others, so you are knowingly putting her health and life at risk by screwing around on the side, especially with risky hookups. You have every right to pursue consensual activities with others, but it's beyond shitty to do that while you're with an unknowing partner.

On another topic, if being a sissy sub is what makes you happy, you'll have to figure out how you can live with it. You may need to be open to moving to an area that's more tolerant of diversity and has a good community you can seek support from. Tough, but people do it well daily.