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Dude, I'll offer some insight for you. My first experience with a ladyboy was in 2004. I was 21 years old and was dating a Filipino-born ladyboy in Chicago, IL where I live.
I had been obsessed with shemales (particularly asian and latin femmeboy types) since high school, but I had never acted on any of my impulses and only dated ggs.
I know what you mean about your concerns, because I had a few of them myself. I know a few guys who slept with a LB and then regretted it, feeling guilty (a product of Catholicism probably ).
But anyway, I just went for it. She came to my apartment after a date one night. I had never sucked a cock before, and I was nervous because I didn't know the size of hers. She was my first, and I really wanted to have a bigger cock than her (some sort of macho bullshit that I'm now completely over... in fact I'm turned on if the LBs I date have a bigger one than me now!).
Anyway, I made a move, and ended up giving her a blow job. Sucking her dick was the most amazing thing I'd ever done with anyone sexually. Just remembering it now makes me super hard. After I blew her, we fucked. I was her first boyfriend in America. We lasted 7 months together before she ripped my heart out (wanted her freedom to date and sleep around).
Probably still the most significant relationship of my life.
Long story short, don't worry about that guilt/repulsion you might feel at first. It'll pass and you'll be a more experienced person. Just go for it, man.
Oh and my next date with a LB is Halloween night... and she's already promised to make me "cum hard."
(hardpaolo @ Oct. 23 2008,13:41) Not so much a sore issue, just funny when guys say they want some cock but they are not gay. It's defensive and dillusional. By the way i'm not gay.
Hmmm, "defensive" I might give you that (hey it was my first post!)
But "dillusional"?
Look, I'm not here to sort out my sexuality -- I'm very comfortable in my own skin. I've only dated / have been with GGs my entire life. Never close to a "gay" encounter. Never been curious to find out what it would be like to have "gay" sex with another "man".
But as Seinfeld said "not that there is anything wrong with that". I am very much a "live and let live" type of dude. As long as its between two consenting adults, who cares?
The "3rd" sex to me is the last frontier -- it gives me the most excitement. I'd never be with a "man" straight up and the thought, frankly, repulses me.
But a gorgeous, tight, sexy, feminine LB? Nothing hotter IMHO. Nothing gets me harder, faster than the thought of a sexy LB.
Does that make me "gay"? I guess it depends on your definition. I like one of the posts I read in one of the link provided above. To view sexuality in a harsh black and white dichotomy is way, way to rigid.
There are degrees of sexuality -- i.e. a GG can, on one extreme be very "butch" very "masculine" and by the same token, a guy can be very "girlish". There are shades of grey. If by gunpoint, I had to choose to fuck a GG who was hairy, muscular and more butch than an NFL linebacker or a very "beautiful" LB who had been on hormone therapy, breast augmentation -- the whole nine yards, and fully clothed would fool 99.99% of the general population -- and I chose the LB, does that make me "gay"?
The other thing I'll add is that I think there is a very strong correlation (just an observation) that those into LBs tend to be very highly sexual people.
I know that I am. I am a downright horndog. I think about sex almost 24/7. When I am walking around outside, I am always scoping hot chics. I am undressing them with my eyes constantly. To me, there is nothing more pleasing to the eye than a beautiful, leggy sexy girl who dresses to kill. I love it.
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