Am I Thinking Too Much?

[BottomKink]

Ever since I started having sex with men, I have always been a bottom and never thought twice about it! My first top was a stocky trucker, and since then I continued to seek men with that similar bodytype everytime I cruised for cock. I never thought too much about how "passable" or "femme" i looked because I had a really good success rate in scoring NSA cock just by dressing normal. Okay, sometimes I wore black tights to show off my ass, but not all the time.

Everything was okay until I hooked up with a guy who pretty much made love to me instead of treating me like a cum dumpster. I would suck his cock while he was sitting down, and at times he would lift my head up, look into my eyes and tell me how sexy I am, then kiss my neck!  When I took his cock missionary, he would move slowly in me then kiss my legs. It was easily the hottest hookup I've ever had. Then I started questioning whether I should have transitioned into a woman during my teens like Bailey Jay. Or at least taken hormones and gotten fake breasts. 

I know its not a requirement to go to that extreme just for NSA cock nor does it guarantee a higher probability of top men whipping their cocks out for me, especially since the porn centered around the men I hook up with often involves a hairy top stocky bear fucking a hairy bottom stocky bear. But, what if I end up being in a (very open) relationship with a guy who wants to dress me up, but then looks at me as if I'm not pretty or "passable" enough for him? Should I just stop thinking too much about having a super passable femme appearance and just continue being a good cocking sucking faggot, or should I attempt to be a really rich guy who offers to pay for a complete transition surgery in exchange for whatever he wants?

[drscorpio]

You are conflating two things in your head: being a load-taking cumdump and being trans. You may be both of those things, but they don't automatically go together. As you already know, being able to present as a woman is not necessary for making top men happy. If you had feminine breasts there would be some tops who would find you more desirable, but they would also be a turn off to some tops. Of course, there are plenty of tops who would not care one way or the other. As you said, it is not a necessary thing for taking lots of loads. 

If you honestly feel like you may be a transwoman, then you need to discuss it with a sex-positive counselor. 

[BottomKink]

I don't think a sex-positive counselor could help me. She'd probably label me mentally deranged after I tell her how my problem started and what I did about it lol.

I've always had a lingering feminine side ever since I was a kid, and it came out of me when I first had sex with a man. Then my femme side increased each time I got better at seducing men, sucking their cocks, and making "girlie" type expressions to them. And since I never had a learning curve in terms of sex, the idea of making that full transition into an actual woman is probably the next step in becoming an actual sissy bottom girl! 

Breasts aren't an issue. I have noticeable breasts and virtually every guy that fucked me doggy style always leaned foward and squeezed my tits. Even a couple who fucked my missionary leaned into me with their palms placed firmly on my breasts. Making the transition would be a huge and important step, but the NSA m4m scene is pretty much dying, and it's pretty much dead online. So I'm probably better off leaving things the way they are. 

[claireannet]

On ‎1‎/‎30‎/‎2017 at 6:16 PM, BottomKink said:

I don't think a sex-positive counselor could help me. She'd probably label me mentally deranged after I tell her how my problem started and what I did about it lol.

Some may suppose, based on my screen name, that I am fairly fem.   Although I do not talk about it much on this site,  I am actually in transition.   Both my doctor and my therapist have been huge help.  And despite your comment, their goal is to HELP not to label, blame or discourage.   Rather they are focused on assisting me with my mental and physical health as I make some significant changes.  Even as I ***** ******* (*** converted to POZ) they were helpful (although very straightforward in their thoughts and beliefs on that subject).

If you are serious, find a good supporter in the medical community.  I believe it is an important part of figuring out a complicated path.   

[gwmxyz]

64 域多利道, 由西寧街進  Kwong Ga Factory Building 廣基工廠大廈    

I know nothing about this sort of issue, but that’s never stopped me before, so here goes.  First I agree with what's been said  about finding a ‘supporter’. Complete tossers are in are found in all professions.  Why do they become doctors?  I don’t really know.   I once read a restaurant review which began  “I’ve said it before and I’ll say it again, some people are not suited to a career in a service industry”.  It’s pretty obvious, but we’ve all been to that restaurant.

But even if they’re not complete tossers/in the wrong job this still might just be too much them. They’re well meaning, its just too far from how they see themselves. I once read an article by a qualified intelligent doctor who thought the appeal of bareback sex was that people didn’t like the hassle of condoms.  It was just a practical point like having a spare tyre in your car and knowing how to use the jack.  A nice person - she wasn’t saying how the hell-fires are being stoked for us now - but just didn’t get it.

Almost anyone who goes into medicine can imagine working with children.  Its fun, they recover from illness and we know what its like because we were all children once ourselves.  The most impressive doctors I’ve met are at the other end in geriatrics - an odd choice you might think. Their patients all die and there’s not really that much they can do about it.  Or so you might think until you’ve met one. 
And this is less mainstream.  My guess is that it gets some very impressive people, but they will take some finding out.  It will be obvious when you do.
And whatever you do, don’t worry at all about people thinking you’re mad. It doesn’t matter.  My answer to “are you mad?” Is “I don't know but I’m happy”. I suspect neither of us are, but if it is a choice then it’s definitely the one to go for.   
Not least coz it’s what pulls the guys.  It is impossible to make yourself the perfection which “guys like”.  What guys like is too different and too contradictory.   Starting with the obvious,  we don’t mean all guys, we mean a small subset of them. If it’s all  career and their right hand - I’d leave them to it. 
As Paul Simon said - “She looked me over and I guess she thought I was alright.  Alright in a sort of a limited way for an off-night”.  We’ve all been there.  Bad sex isn't dying - it's always with us. So how much bad sex do you swap for even once that's great.  Where even the thought of it makes you hard now?  I’d work on that - what's right - for you.  Don’t worry about anyone who thinks you’re mad or any amount of bad sex you’re missing out (probably with them) in the meantime.  Get it right and I doubt you’d be doing too badly for quantity either.  

[einathens]

you're definitely overthinking things. 

you're worrying about what might go wrong with a relationship you don't have with a guy you haven't met.

there are as many steps between where you actually are right now and where you might end up as there are between wheat in the field and bread in the supermarket. 

I know almost nothing about trans issues, but to me it sounds like you're just fetishizing the behavior in the hope of perhaps being more desirable to an unknown partner at some unspecified point in the future. 

you've got a lot of issues. my advice? pick one, any one, and work on it. then pick one more and work on it. and so on. 

personally, I'd start with the fact that it freaked you out that a sex partner treated you like a person, and not like a receptacle.