First time Encounters while dressed

I have been fantasizing more and more about being with a man while dressed. The desire has grown to the point where I am seriously considering planning an encounter to satisfy this desire. I?m nervous as hell as when I am not Josephine I have zero desires to be with a man but as Josephine the urge is so strong that every dressing occasion has to end with that fantasy in my head.

I am wondering if anyone else here has experienced this desire, how they have handled it and if you have taken the plunge how was it? For context My dressing has always been a private thing. I dress for me, in private and have had no desire to be out in public in any way. So this desire to express myself with a man is a little weird to me. I?ve considered sharing with another cross dresser to sort of have best of both worlds and experience my dressing with someone who totally understands where I?m coming from without judgments.

Any thoughts or sharing of experiences are welcome.

Sometimes its best to leave a fantasy a fantasy than actually act on it and be very sorry later on.
You are dealing with another person's feelings or interests.
I would say that fantasy its quite common among CDers.
I came out as gay many years ago so I knew what it was like to be with a man before I went 24/7 and HRT.

I must ask are you married?
If so then it would be cheating wouldn't it?
What would happen if she found out?

are you married? what would ur wife think?

if i guy wants to have sex, its so much easier ro to have sex with another guy.

if a cd wants to have sex with a guy, its even easier. so easy to find a guy that will worship a cd.


if you are watching cd and male porn, lay off it for a while and I'm sure your urges will.go away.

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Originally Posted by TAG

Sometimes its best to leave a fantasy a fantasy than actually act on it and be very sorry later on.

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I totally agree. That is why I do not own a wringer washer and a cow milking machine ! Lol.

I see from your other posts you are married and she does not even know of your cding .
I have no words. ( or ones I can say )



There is a post in Loved ones that talk about this subject
Have a look.

Wifey and Hubby Have a Talk: Of Heterosexual Men Making Love With Men

I have the same fantasy but have left it a fantasy. I?m not sure if as Ashley I am truly attracted to men or if the thought of being treated like a woman by a man is what I?m attracted to.

Thank you, Ashley, that is my concern as well. Is this just a fantasy and will reality be something really different. Is this impulsive? And yes I agree about the suggestion regarding the porn. I think that does play a role in adding fuel to the fire. This has been tough as I?ve been in this journey by myself navigating these waters and now I?ve come up on a tough one. I appreciate everyone?s thoughts and suggestions.

Fantasy & reality are two things that usually do not mix well together.

I have thought about it too, but the thought of some big hairy man using me as a sex toy is a total turn off.

Again, the fantasy is probably better than real life!

Jo, for 10 years a dealt with fantasies of being the woman with a man. I was sure I'd turned gay!:eek:

Then, I realized there was NOTHING I found attractive about males or they're parts!:doh:
My fantasies stopped soon after! :thumbsup:

A fantasy is one thing, a plan to have an "encounter" may be very dangerous for you just to "satisfy your desire". There have been documented horror stories when someone meets a stranger for more than a casual encounter. Not only is there a possibility of physical harm, but you may also share some dreadful, life long, disease with your wife.


I will echo what Di has to say:

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I have no words. ( or ones I can say )

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I agree with those who say "lay off the porn". It's not real life.

I have been hesitant to respond in this thread, but I have to agree with many of the others. You need to keep this purely in your fantasy land and porn is definitely not reality. To be honest, this site has sort of replaced my porn habit meaning I have very rarely looked at porn since coming here. That is not to say that this site provides any overt sexual gratification, moreso that I find I don’t need the activity like I felt before and reading on here is more interesting and educational than just the physical activity that watching porn led to.

Oh and despite what some may protest that I am fooling myself, I refuse to believe that the majority of cross dressers have this fantasy. Not that I am judging negatively or implying anything is wrong with it, just that it has never once entered my mind. Yes, cross dressing certainly has a sexual piece to it, and up until recent months was sort of my primary focus about it, but as fun as it can be to pretend to be and look feminine I have zero desire to be with a man or experience that in any way. Again, that is just me, not saying it isn’t okay for others.

I don't have experience as the CD looking for the first time encounter so I can't help with that. What I do have is more then a fee times being the first encounter for the CD. As you said many think the same find another CD or Trans girl and get the best if both. After weeks or months of the oh I'm a dirty —-I want to wear sexy things and stuff. If the CD ever actually shows up there is a lot of hesitation and second guessing. If anything does happen it is very short lived. I dont begrudge anyome their fantasy or desire but from your post alone it won't be what you are building in your head to be. Keep the fantasy if it makes you happy but it would likely be a waste of your time to try and presume it. There is a tin of nerves to get over jist to get there dressed to even consider the rest of it. And being you said it's a private thing that would take a lot out if you.

For me, sexual fantasy is a strong component in my desire to dress, and in a way dressing itself becomes a method to live out that fantasy. This fantasy and living out at least a part of it through dressing seems to have filled a large gap in my psyche, no doubt an experiential one. I recognize that will have to be enough - but given the opportunity to go further, what would I do? Would I live out my fantasy to the fullest? I don't have an answer to that question, I've never been hit on in real life. But I do know my fantasy - and my alter ego - allows me to go right to that edge, and it is very pleasurable indeed.

So Josephine, I think I know exactly what you are talking about.

Reality check. From what I've read you're married yes ?
Having sex with anyone other than your partner in a monogamous relationship is really vile behaviour.
If you want to have sexual relations with anyone else then leave your partner. I abhor people who cheat, it's a cowards way of not dealing with the real issue.
Keep it as a fantasy, or act on in when you are single (which if you're asking people on a forum whether you should enact it will probably be soon)
Seriously.

Gay bar or mens club comes to mind if it's just the sex your after.
Gay bar you might be hanging around fishing for a while, might even end up having a relationship, mens club you could be done in an hour (maybe visit and observe the first time or two to see if your comfortable there).

Here in NZ, visiting such places would cost me my marriage, family, friends and 50% of our current assets.
I think over in the US it can cost you everything you have... and years more of payments?

When I was young, I was never interested in such an adventure, as my body aged and my T lowered, it has become a fantasy.
Thinking about Porn, what they call the "money shot" is because our bodies are hardwired to copy such action and it's gives us joy, so why wouldn't we want to see it "live" or be an active participant?
We don't because of social / peer morality (and cost) that is part of being a member of the Heterosexual group.
My gay friends mostly tend to have "open relationships", which is how and why these places are financially viable.

You're married?
Sexual encounters of any kind with anyone else is cheating.
Don't do it.
Simple enough, don't you think?

Reading those threads where a member casually throws in the fact that she is going to cheat on her wife is a schizophrenic experience. There are two threads in one. The one in which people appalled by the cheating are trying to offer the OP a reality check, and the one where the OP and other members blatantly ignore the elephant in the room (because they don't judge? Because they approve? Because they were distracted reading the previous posts? No idea) and keep the discussion going as if everything was normal in the finest of worlds.

As a male i have no intrest in outher males as Wendy i have no intrest in males but have intrest in women so my males side is straight my feminine side is gay

To our judgmental sisters: Not everyone is in a wonderful monogamous relationship. Not everyone shares your moral compass. Not everyone sees the world as you do. Let's not forget that the world is full of individuals who think we are freaks or degenerates, simply for being who we are. Embrace diversity in all its manifestations.

I'm sure fantasizing about a sexual encounter runs through everyone's mind on occasion; husband with another woman, wife with another man, gay or lesbian curiosity, etc. In most cases the expectations exceed the actual event. If you're totally in the closet with your wife when it comes to the cross dressing issue, threads like yours scares the crap out of wives. Keep your fantasy to yourself and don't act on it.

My first few encounters with men were a bit awkward, mostly because I had no idea what I was doing or how to be a bottom. Took me a while to learn the mechanics of it, what things to do to prepare beforehand to maximize the experience (this is really the key), what I liked, etc. IMHO it does take a bit of practice to make it really enjoyable, but once I learned, omg so fulfilling I can't see ever turning back. PM me if you need more specific info.

Can't say I'd recommend ever going behind a partner's back, but I know many of you are living in a situation I could never imagine. I live pretty openly as a feminine bi/gay bottom and any girls I've dated know all of that going into the relationship. Some have been ok with letting me having sex with other men, but some really wanted monogamy which simply was/is not for me.

Diane, I think its because hardly anyone reads any other posts but their own and 1. Gets so mired down into fantasy that I think they'd urge them to do just about anything they WISH they could do or 2. They would enjoy seeing OP live in the same personal level of hades that they do ...

Anyway.. I'm not being judgmental at all and with what I do for a living every single day- I have no moral compass lol seriously now ...if you all want to do this and theres no stopping you ,fine, just at least be kind and let these ladies go be with men who dont behave like this OR at least let them have a chance to see others also while you're doing your thing ie: open relationship...

I don't care what people say we all judge each other to some degree so by saying you don't judge others well you aren't being totally honest.
To the OP how would you feel if your wife cheated on you with another be it man or woman it doesn't matter.
My two marriages ended because of them cheating on me and both times it was devastating.
I have been in open relationships too and those never seemed to work out because when they are out banging other people and could be with you shows they really don't care about you.
To them you are just warm place to stick something when they choose, you have no say in the matter.
Me personally I can't live in a relationship where I don't matter.

Monica, although I don't support what you do and being married, it is your situation, your choice, and only you and you wife will have to deal with it at some point. I am fairly certain if all of us opened up our homes and showed the rest of the world what goes on behind closed doors there would be a lot of critics, and I don't mean just the CD'ing!
I am far from being critical of others. I probably will speak my mind, but add it is their life to do as they please.

As to the OP and thinking of a possible gay sexual encounter, just think it through, and be careful! There is a lot of seriously weird people out there!

To the OP: If you haven't had any interest in men otherwise, I think this may be more a fantasy about you being a woman than you actually wanting to be with a man.

And for the record: Lots of people have fulfilling, loving, open relationships. Being free to go "out banging other people" doesn't mean that we don't care about our partner(s).

Dana

OK, first I have not read all the other responses, still my $0.02 response....
Poster has only been on the site for a short time, and this is their 6th post, so ?????
Still, My point of view, if they are not phishing......
The poster is +- 50 years old, so much younger than I am, still if they are being honest?
I can sympathize with their emotion. As I aged, I feel the decrease in (MY) testosterone has opened me up to......
Well let's say, now-a-days my thoughts and dreams are nothing like they were 20/30 years ago.....
Now-a-days my dreams are, well 50 shades of....... Gray or even orange..... Maybe Red / Pink or 'Blush'....
Back to the post, my response would be, if you Love your partner, and desire to not destroy your relationship.
Then you need to express your desires and try to keep that person involved in your journey through life.
I can feel that same emotion, still I have not done anything that would destroy my relationship with my SO.
Good Luck. Do think long and hard B-4 you act on desires..... Desires have consequences once acted on......