TS Dating Gude America's Foremost Transgender Woman

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The Ten Best Options for Guys Seeking a Transsexual Girlfriend



Over the years, I saw some guys develop long lasting and successful loving relationships with their transsexual girlfriends. Based upon these observations, I noticed several unique paths that can result in success.

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However, almost all include some “give and take” - like we just discussed. Being realistic from the onset improves your chances for success.

Additional chapters Included in this section, include:

Transsexual Girlfriend: Picking a Match
TS Dating - How to Find the Best Match
TS Girlfriend Dating - The Ten Best Options
Transgender Dating - Common Mistakes
Tranny Dates - How to Succeed
Shemale Love: What's Most Important?
TS Dating: Answers to Common Questions

Go Through Transition with Her

Some of the best and healthiest long-term unions I witnessed were guys who connected with and dated their transgender girlfriend when she just started her transition. A “young” girl - if you will. Sounds logical, no? Thus, why don’t most guys into trans-women do just that?

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First off, a “young” girl in trans-years - often means she still looks like a guy unless she’s done up completely. Some men? They just can’t handle that. You’ll need an artist’s eye for what she can and will become. You’ll need to be “okay” with friends and family viewing you as being with a man. You’ll need patience - going through transition and the related insecurities are oftenbrutal on everybody.

Early Stage Gender Transition

You also need to find a gal that will stick to it. Two men I know made this commitment with trans-women that subsequently decided not to go further with the changes. One such couple is still together after twenty years - although they’re only intimate when she transforms. The other couple is more miserable having never fully dealt with each person’s needs and wants.


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Supporting a gal through her transition requires patience, love and a willingness to see her as a beautiful woman regardless how she looks now. It helps - if you really like the person under the make-up. Alas, that’s ideal regardless of circumstances!

Live at Trans Clubs

Years ago, the absolute best way to find and connect with a lovely transsexual woman was by frequenting trans-friendly nightclubs. Back then, it wasn’t very safe for transsexual women to frequent straight clubs and most congregated together at such spots each weekend.

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Today - with transgenderism having achieved much broader acceptance, very few full-time transsexual women socialize at trans-bars except to occasionally stop-in and visit old friends. However, there are lots of part-time girls around just gaining their confidence in getting-out plus some transsexual women who work as DRAG performers at such clubs.

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Some guys - if they visit often enough and become part of the “family” - end up finding an ideal transgender girlfriend during that process.


Buy Your Way In


I’ve seen a couple of guys who had the resources buy their way into a successful relationship. Both - were very smart about it. They spent as much time looking for a quality person under the trans guise as anyone else. They knew - if you throw money on the table for anyone - the crooks are the first to grab it.

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After narrowing their selection and deciding on their ideal match - they now help financially support these gals and do occasional vacations together.

If you’ve got the resources and look hard? You’ll probably find exactly what you're looking for: just reality in a capitalistic society.

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Become Active in the Transgender Community

There are numerous community gatherings - the largest is
SCC - which is held each September in Atlanta, GA. These functions are a great opportunity to meet a wide variety of trans-women. Most are part-time cross dressers - but you’ll gain a far better understanding of the life and death of the transgender community. If you return year after year - you tend to develop associations and friendships that might blossom into something more.

Transexual Dates

Look Overseas


I met two guys who found their ideal TS wife by looking overseas. This option offers big pluses and some equally large drawbacks.

On the positive side? Stealth occurs almost instantaneously when we get outside our own culture. Translation? Brazilians can quickly identity a transgender woman in their own country - but if she moves here? Her ethnic features tend to cause her to become completely passable almost immediately. Also, certain cultures - like asian & latin American - start with a more optimal platform for a gender transition: smaller frames, less body hair, etc.

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The drawbacks? If don’t speak the native tongue or travel there on a regular basis for work - this rarely works out. Most sites that promote such dating connections are littered with gals just trying to extract money.

There’s a few sincere gals interested in finding an American husband from just meeting on-line - but its rare.

Shemale Love

Develop a “relationship” with an escort

A few girlfriends of mine that work as paid escorts ended up eventually falling in love and dating a former client. Most try to keep John’s at arm’s length but if they just had a break-up and they like the guy - some end up dating.

The hardest part for guys in this situation. Dealing with her ongoing profession. Some promise they’ll stop but fear losing their client list and the financial independence it represents. You also usually had to have invested a good bit of time and money into “paid services”.

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Get Lucky


Luck is often defined as: where preparation meets opportunity. If there was ever a subject where this definition applied? It’s transgender dating.

Why’s that?

Because you might get lucky and meet the girl of your dreams in the most unlikely of places. However, such good fortune usually won’t smile on you unless you’re fully prepared: you know hot to spot stealth-like trans-woman in public, you learned what to say and not say, you determined what would work for you. In other words? You’re prepared to take advantage of the opportunity if chance sends her your way.

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One couple I know met this way: at a straight bar - “out of the blue” encounter. They’ve been together six years and counting.

Lucky would also apply to finding an ideal candidate on-line who happens to be “single and looking” when you reach out. Timing is everything when it comes to love connections. Again, developing your skills and insights with dating trans-women improves your luck.


Stick to Part-Time Trans Girls

One option I see more guys finding fulfilling is to stick with dating part-time trans gals. Such trans-women are almost always fully-functional since they’re not on hormones and they’re much more willing to explore a NSA - “No Strings Attached” connection with guys they like.

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However, just because their part time - doesn’t mean they’re easier to get. Most are only attracted to other transgender girls.

The DRAG Queen / Gay Guy Route

Dating a DRAG Queen
If you’re able and willing to frequent the transgender nightclubs, you might find yourself interested in a DRAG performer. Lots of TS women perform at DRAG acts as a way to make extra money. However, most performers are gay guys who create a feminine illusion for stage.

They know - lots of straight guys end up attracted to their character. If you’re a hot guy - and could deal with having a relationship with a femme-man - this might work for you. Most gay DRAG queens that date such guys are sensitive to his need to only see the girl early on. However, she’ll need you to embrace and love the fact she’s a man with no intention of becoming female and usually with no desire to dress feminine in the bedroom.

Stay with Paid-Fun & Fantasy

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Speaking of “reality” - sometimes its overrated. If most of your desire is sexual based, you’ll probably be much happier keeping this leaning primarily in fantasy world.

Translation?

Enjoy your pornography safely and soundly in the privacy of your own home. Perhaps hook up with a professional transsexual escort once each year to augment those dreams and visions.

TS Love

In fantasy land? Everybody’s beautiful, there’s no foul body odor, nobody steals your money, none of your friends judge your lifestyle, etc.

Is that really all that bad?

Sometimes, what we have now? Its more fulfilling than we give it credit.

Become an Active Cross Dresser

A lot of guys who want to date a transsexual are privately fetish cross dressers. Thus, much of their attraction towards a TS partner is rooted in the fact they privately fantasize being her.

If this circumstance is you?

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I would strongly suggest you more fully explore your desire to cross dress. Most of you don’t go further in this regard because you’re mistakenly convinced you could never look decent as a woman. You’re wrong! Every guy - with the proper transformation tools and skills in hand can be made to look like a woman. You first acquire those skills by getting a professional makeover and transformation by those artists skilled in working with transgenders. If you visit my “
Crossdresser’s Survival Guide” - you’ll find tons of information to help get started.

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I can’t begin to tell you how much happier you’ll be going down this path versus trying to develop a relationship with a TS woman if this is your reality. I’ve seen this countless times over the years and heard guys subsequently muse: why did I wait so long?

Guess what else? There’s lots of other beginning trans-girls who are only looking to hook-up with other cross dressers. Thus, your likelihood of sexual fun is enhanced as you grow in this regard.