I'm looking for stories of "fringe" "out there" "weird" and "extreme" hobby experiences. Please share.

I'm pretty boring but I have had a few experiences a little outside of the norm although I would not necessarily say they're weird.  

Been with a couple TS...3 girls at once a few times although I prefer just 2...was 1/5 of a group of guys who 'competed' with 1 lady (she won!)...a few things probably illegal in many places...BBBJCIM under water...

Guess I'm unclear what you're looking for.

Hi OldTimerB.

Those all count!  

I've always been curious about the TS scene.  I consider myself a straight guy with no bi-curiosity, but then again I've seen ads for a few very convincing looking TS ladies out there that honestly made me reevaluate for a second.  Is this something you got into due to "boredom" or what attracted you towards it?  Have you ever had gay sex or relationships?  This has always fascinated me.

Sigmund
 

had a girl mess with my Superego and my Id...

While not for everybody there are MANY beautiful TS women who (I imagine) would easily pass for all woman with an added bonus & my thought is a guy who goes that route isn't necessarily gay or Bi at all -just curious......
               A man who has a gal "peg" him sure doesn't mean anything about his sexuality -IMHO,
so I'm wondering how those who like the TS scene identify ....how do you view yourself, BI, or maybe try ( try-sexual)  

 
Anyway great topic all around thanks for starting it, I'll be watching 4 some good replies  

I have just begun the trek into T-girl territory.  I'm not sure what attracted me to it.  I, like most men who are attracted to the transgenders, am a completely straight male.   The ladies have to be convincingly feminine, or I can't go there.  So far I've just tried it once, and it was a mixed bag, but that was mostly the lady's fault.  Anyway, if I had to venture a wild guess as to why that particular scene started to attract me, I would say it's either because I don't get enough sex and I need something extra "naughty" to make up for it, or maybe it's because I'm rebelling against my religious past and church people would consider that type of behavior to be "gay."  In fact, here's how it happened:  I was a new "deconvert" (from Christian to Atheist), and I started to wonder if there was any chance that I was bisexual.  So I went to a porn site and watched about 30 seconds of gay porn before I started feeling ill and realized that I was not at all bisexual.  Then I noticed a "shemale" link, and lo and behold, I got turned on.  I then proceeded to check out TransExotica at the Gay 90s, and...well, if you need any more info, just read my reviews

I'm straight and completely attracted to women. I enjoy a strap on now and again (it's hard to determine providers who are into this). While I haven't explored a TS, I think it would be fun.
In my mind, it's about the fun and the feeling.

Mindy,

This is a little naive if you think all gals (assume we're talking TS here) "peg" the guy as you put it. In my case, I can neither confirm nor deny this.

That there is any: "all" or "every time" about any such thing concerning guys gals or TS individuals.  
I do my best not to make  all encompassing statements or assumptions
 and certainly never meant to come across that way.

All I'm saying is -personally I've never thought of pegging or visiting a TS to mean one was bi or gay because of such a visit or act.

So ehem........... am I being understood now? or maybe you just get a kick outta misunderstanding me  
Either way here is a disclaimer:
I, in know way, think I am perfect  
and I'm sure I'm probably naive about a great deal of things that I don't have much experience in  
and I'm perfectly ok with that!
Have a happy day  -- Modified on 8/29/2015 5:09:03 PM

That was a poor choice of words when I said "all" as I know you weren't talking about that.  

I just thought you seemed to associate "pegging" with TS gals. To me, that's like my associating FS ladies with anal or something. I just thought you could have worded it a little less absolutely.

Regarding getting a kick out of misunderstanding you, sorry but no, you're just another poster here to me.  

I neither like nor dislike you as I'm just responding to what is written and how I interpret it. Whether the way I understand it is correct or not would likely be determined by how well you (and others) get your intended point across.  

If I didn't "get" it the way you intended, maybe it could have been said in a clearer way perhaps? That obviously applies to everything I write as well as everyone else of course. There's certainly been enough "misinterpretations" of 'intentions' recently eh!

For fucks sake...really?  So...ehmem...yes most of your post come across as condescending.  If you were trying bless you as you won.

from the agency, exited my vehicle and cops descended on the hotel from every direction. Turns out they were  
chasing a guy who ran thru hotel. Freaky!

Back in '06 I met this incredibly hot young gal at her place downtown. She had an extremely nice little condo, and it seems that she must have forgotten it was up on the market. In the heat of the moment, my ass pumping up and down, mirror across from the bed, well you guessed it. In walks a realtor with a couple to show the place.  She shot out of bed grabbing a towel and asked if the realtor could come back later, to which she said sure. She returned to bed and we laughed so hard. The date finished off in excellent fashion. The weird thing is this is the last time I ever saw this lady advertise, hmmm suppose she got the sale???

END OF MESSAGE

My first thought after reading this was that maybe the gal you were with didn't actually own the place, and that she was actually a realtor too...

Holy shit, there's a great scam here!  Think about it, if you were an escort realtor, you could call someone and say you have a client who wants to see the home, the owners of course will scramble around to get our of there, you show up with your client, do the wild thing in a free house, and leave.  Why haven't I already thought of this!!!

...show me some properties and use the opportunity for a quick romp in someone else's house. She had just the fun, playful vibe that I bet she'd arrange that if I were to ask.    Hmmmm.....

Some of the freakiest experiences I've ever had have been in Rochester, MN.

Okay, before I even knew about "escort life".  I lived in Rochester for about 7 months.  I worked at a bakery and at the TGIF on the highway.

I had a Hawt experience with a foot fetishist and also...  I was approached by a Dr. from Egypt one afternoon as I was walking to work.  He picked me up, dropped me at work, showed up at end of shift and drove me home.  He started paying me for "allowing him" to drive me home.  Then he paid me for touching his penis while he drove.  Then he paid me for lot's of different "favours".  

That was kind of sexy.  I liked him anyway, but he always wrote me a check... ( this was back in the nineties) when I touched his cock.  Makes me smile now.

But anyway, in my life as a sensual massage therapist in the early 2000's, I was asked by a potential client to drive to Rochester, where black leather, and wear black thigh high boots, and meet him at a certain hotel.  He wanted me to spank him, spit on him, and then go away.

Over the process of a few weeks and many emails, I realized that he wanted me to black mail him.  He wanted me to extort him and our experience.  He wanted me to threaten to expose him to his wife, his employer, his charity work, his church.  He wanted me.... wanted me to extort money out of him.

Honestly??? I couldn't do it.  

So he set up another booking and he wanted me to beat him, to take the cash out of his wallet and threaten exposure if he didn't give it to me.  He showed up at our booking with over 2000. in cash.  He begged me to threaten that I would call his mother if he didn't give me the cash.  Then he gave me his mother's phone number.  !!!  

Now... that was the strangest it has ever gotten for me.  

That same afternoon, I was driving back to the cities from Rochester and got a call from my little sister that she was seriously considering becoming a nun after having spent two years at St. Kates College in St. Paul.  And she wanted my opinion......  

Yeah... strange!!