my first time w/ trans

[ocinteeni]

So I knew that I would never feel at peace until I took my fantasy and attraction to transexuals to the next level and experience sex with a transexual.

So I took it upon myself to make it a priority in trying sex with a transexual. Unsure of how to go about this since I personally know absolutely no transexual women I went on craigslist, which I know is has a reputation of sleaziness but I had to try somehow, right?

So I decided that my trip to San Francisco for a music festival would be a good opportunity to make this happen. I sent some e-mails out got responses from about 3 and one seemed like they were legitimate and serious, not faking or anything. We talked on the phone planned to meet at her place and finally what has been brewing in me for years now, starting with curiosity of looking at transexual porn to exclusively looking at transexual porn and fantasizing about seriously being with one, was about to culminate in this one sunday afternoon in San Francisco.

I am going to give fair warning if you like reading these for some juicy details to jerk to save your time and quit reading, this isn't gonna be like that at all.

So to begin with when I was sent a picture of her, it seemed sort of questionable, like it might just be stolen from some girls myspace or something. Well anyways after the fact I'm almost 99.9% certain that it was not a picture of her, and she was more of like a CD not a transexual. Which really was absolutely disappointing for me. She said she was 26 but I'm certain she was like 30 or more. I was almost 99.9% sure she was wearing a wig, and I don't even think she was taking hormones, her tits didn't look hormonal, more like really physically undeveloped somewhat flabby guy tits. She wasn't even totally hairless, and I know some of you are gonna be like who cares, but I mean she had hair all in her ass crack, which to me is such a huge turn off and she even had some little tiny nipple hairs and a little happy trail going on, fucking disgusting!

Now some of you are probably thinking how come you didn't get a good look at her at the door and just book it on out of there. I will say that I was so determined to have this experience under my belt because I felt like I needed to understand my sexuality better, that I was overwhelmed by it actually happening and I just kept going with it even though in my head I was thinking, "wow I dont find her in the least bit attractive." Also, this is a really nasty bit of information that many will be thinking is "too much information" after pulling out when having sex with her, there was a little but of her crap on it, that image has been haunting me ever since, I am so freaking disgusted by it, it makes me feel terrible even writing about it now.

I feel really disappointing with the entire experience and I would prefer to forget it ever happened. I know that in no way should I even think about holding the girl responsible for how I feel and I never will hold hard feelings to her. Even though she was absolutely misleading on craigslist I really blame my stubbornness on acquiring this new experience and my lack of a back bone for not speaking up and saying something like "sorry I think we aren't for each other," for the way I feel now. I see that what the case is, as for many of the guys on these forums, is that we have built transexuals up in our fantasies so much that if or when we are confronted with a reality of it we are subject to be absolutely disappointed. I honestly don't even know what to think of what happened, I just knew that I had to let it out somewhere, despite if it not being a great story for any of you to hear.

One thing I know is that I still want to have a experience with someone who I am actually attracted to. I have learned from this experience that I need to be strict with what I am looking for in a sexual partner or in a relationship.

feel free to say whatever comes to mind, i don't be shy

[ocinteeni]

the only thing I can add to this is that throughout this entire experience my friends where behind me 100%. Friends that are absolutely not into and do not entirely agree with the fact of transexual women. They were aware of my plans, are aware of what it means to me, and are absolutey happy for me that I took the necessary steps to try and fullfill what I am looking for in my life.

[welshie85]

Dosent sound like a nice experience!

[Bionca]

I want to say a couple things. First, it is very important to make sure you have chemistry before having sex. I understand this was during a trip, so time was probably an issue.

As far as the girl you met. She sounds to me like she may have been a CD or likely a gal early in transition. Hormones won't stop nipple hairs, and quite a few GGs have them as well (they just pluck them), for some reason and a slight "happy trail" is also fairly common with GGs as well.

You were there, so you have a much better assessment of who she was and how she presented herself. I'm just giving you what popped into my head.

I think you are also quite correct that building anything or anyone up as a fantasy will only make the reality - well realistic (and not nearly as fantastic). Ans well.. it was craigslist... :p

[Bionca]

the only thing I can add to this is that throughout this entire experience my friends where behind me 100%. Friends that are absolutely not into and do not entirely agree with the fact of transexual women. They were aware of my plans, are aware of what it means to me, and are absolutey happy for me that I took the necessary steps to try and fullfill what I am looking for in my life.

I'm also glad you realize this for what it was - a learning experience. I'm also glad that you are processing what happened and are not (particularly) freaking out. I am a little weirded out about the "painting" of your dick. If there is even the remotest hint that a date would turn into sex, my stuff was clean. I just can't imagine not taking care of that bit.

[ocinteeni]

I'm also glad you realize this for what it was - a learning experience. I'm also glad that you are processing what happened and are not (particularly) freaking out. I am a little weirded out about the "painting" of your dick. If there is even the remotest hint that a date would turn into sex, my stuff was clean. I just can't imagine not taking care of that bit.


is the "painting" of my dick what i said when i mentioned the too much information part? And I know it seams like im picky about the hair, and i understand that girls regardless if trans or genetic get hair in those places sometimes but they are properly groomed, ya know? But the reason why it made an impact on me is because it made her out to be strictly just CD not actually a practicing full time transexual, and I am just not attracted to part time CD's that are CD just for sex and thats the impression I was left with.

Thanks for your input though, it feels way better to talk to people about it that are more understanding, which my friends are but they still are not ideal because they still think its weird and guy friends will really pick on you for stuff like this.

[Bionca]

is the "painting" of my dick what i said when i mentioned the too much information part? And I know it seams like im picky about the hair, and i understand that girls regardless if trans or genetic get hair in those places sometimes but they are properly groomed, ya know? But the reason why it made an impact on me is because it made her out to be strictly just CD not actually a practicing full time transexual, and I am just not attracted to part time CD's that are CD just for sex and thats the impression I was left with.

Thanks for your input though, it feels way better to talk to people about it that are more understanding, which my friends are but they still are not ideal because they still think its weird and guy friends will really pick on you for stuff like this.

The only reason I mentioned the hair and stuff is because she may have been full time, or starting to transition - trying to give her the benefit of the doubt and all. I have to agree that even in the beginning, if I was expecting to be naked, my stuff was groomed.

"Painted" is, in fact, what you were talking about. Poo on the dick. It can happen, but any person bottoming should know how to keep that to a minimum. I'm really at a loss. Actually, the way you describe her, it really sounds like she didn't put much preparation into the meeting. That's a shame really. Back when I was dating and the few times I actually decided it was OK to be some guy's first, I REALLY went the extra mile to make sure I was as darling and lovely as I could be.

(On the off chance he actually showed up for the date, I wanted him to be glad he didn't chicken out ;):p)

[ocinteeni]

ya the hair thing could be she is transitioning, now that i think of it could be a cultural difference too, she said she was from indonesia and she had only lived here for two years, who knows though... oh well...

and well it seems like my first time should have been with you bionca you really know whats up, if only...

[Skeggjold]

You should have just gone for an "escort". If it was such a big deal that you act out your fantasy, 200-500 "roses" is not exactly back-breaking, and "escorts" have to both put up (close to) realistic pictures at their websites, and put considerable effort into their appearance and hygiene, in order to get repeat "visitors" and good press, so to speak. You can at least see if they have breasts, if nothing else.

I can think of one girl in my area (and there are doubtless ten times as many TS "escorts" in San Francisco as in my area) who is something like 200 "roses" an hour who I would totally go for if I had any intention of acting on my fantasy. Not to mention you could set your goals high and travel to New York or Miami when Efe is in town (she is, imho, probably the hottest TS "escort" in the world). Efe would be worth any amount of "roses", again, imho.

As a Post-Script, I hope nobody is offended if I come off as crass or insensitive, but we are talking about sex for the sake of sex - it's kind of hard not to objectify the target of your affection in such a case.

[ocinteeni]

ya unfortunately i have less than 200 "roses" to my name, I'm only 20 years old working part time and going to school so I need that money for gas to get to school. I guess I can't complain then, right? Later on I really would like to go that route, just got to wait for the cash flow.