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Thread: my boyfriend likes to crossdress, and a few other "problems"

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    my boyfriend likes to crossdress, and a few other "problems"

    First off, I am very open minded, and very accepting to all sexualities. "Whatever floats your boat, I'm okay with that." I went to school with a crossdresser, it didn't bug me that he did it, and my best friend is gay. But I digress, anyway...
    (This is going to be a long post) (a little explicit)
    So, I met him about a year ago, and we've been together 7 months. I am his first everything. Kiss, girlfriend, even first date.
    But, a few weeks after we met, I found a dress, in his room, which he had admitted it was for Halloween that year, and he had just bought it. "Haha, that's awesome!" I told him to show me, so he put it on and we both had a good laugh. Halloween came and he decided not to wear it, chose a different costume instead. We got together in mid December and our relationship got into heavy petting pretty early. But one time, he put on the dress and again, I laughed about it, and he wanted me to kiss him while he was wearing it and it escalated long story short, he stained the dress. To me, it was a joke, until afterwards we were talking about it, and he said "it's kind of an addiction" all I could think was, "wait, what?" And all I could say was, "oh".

    At that point I was really confused, but I figured it was a "once in a while alone in my room thing". He hadn't really worn that dress until a couple months later, wore it while fooling around, this time it made me feel like I was a lesbian. Here is my boyfriend, wearing a dress, I am kissing and rubbing him, and all I could think about was the clothing. Because I didn't (and still don't) truly understand it. But I didn't weigh on it.

    But this isn't the end of it, we still hadn't had sex at this point, (which I understood, it was his first time so I know he wanted to take it (kinda) slow. But what 21 year old virgin guy wouldn't even try to have actual sex with their more than willing girlfriend? (I know it's stereotypical, but that's what was going through my mind. When ever I even went NEAR his phone, or tried checking the time, or when he even thought my phone was his, he'd snatch it either out of my hand or where it was sitting. He snatched MY phone out of MY hand thinking it was his. This got me curious, and I needed to see what he was hiding, my first thought was "what kind of porn is he looking at that he doesn't want me to see?" The opportunity presented itself, opened his browser, and I see an anime girl, with a penis. My stomach dropped, he walked in, and I laughed about it. He said that site has everything, and when he was "finished" he just scrolled through pictures. I figured he was just into anime. He had gotten a new phone and still kept that one. It still had internet on it, I joked about it as his porn phone, because I knew that's what he used it for. He kept it hidden, I knew he used it for porn, I don't care that he looks at porn. About a month and a half/ 2 months later, I still wanted to know what his fetish was. So, I looked in obvious hiding places like in his underwear drawer, and then in between his mattress and I found it. Turned it on, pulled up his browser and his history was cleared. Until I typed in "x" on the search bar. 2 videos popped up (I assume as his favorites) one was of a transsexual, masturbating, playing with his/herself (I apologize, I'm uneducated on this topic) and then the other was a group of transsexuals taking turns having sex with a male... all I wanted to do was cry, I didn't know what to think except "it was my fault for snooping" "I deserved this" but I was upset, I went home that night, cried a lot and looked up possible reasons he was into it, and still with me. Nothing shed light on it. I just figured he loved me, and wanted to be with me no matter what. But I still wanted to aid to his needs. I ordered a toy. And before it got there, that's when he decided he was ready to have sex, and we did. But he couldn't get off. He couldn't feel anything. He isn't small, maybe a bit over average, and I've had sex with people before smaller than him, and they never had trouble "getting there". Tried it 2 more times, and still, nothing. I got really sad and insecure, and started crying not understanding, and everything was just overwhelming. I told him what I found on his phone, and all he could say was "I don't know why I look at that stuff". He swore he's not gay, assured me that he thinks I'm sexy and that he didn't know why he can't get off either. One time, we used the toy, He finished, but the thought of it really turned me off. He went to "help" me and All I could do was push him away and tell him I was tired, and tell him I didn't need it, (without being rude). I did this to myself, I know this, so I rolled over, frustrated, and went to sleep. On another occasion, I was alright with it, surprised him with it so he didn't have time to put the dress on, which he hurried up and put it on anyway. I ignored it that time, and was able to do it without getting turned off, and when he was finished, I asked him if it was my turn, and he told me he couldn't because his brother was coming over. And I got frustrated.
    And don't know what to do. He puts on his dress more often, and ordered another dress for "Halloween"this year. I just want my boyfriend, but now it just seems like I have a girlfriend. :/ he never wants to have intercourse, and the only time he does is when he can TELL I'm needing it. At this point, we've had sex 4 times. And I have used our "alternate methods" on him over double that, and it's really making me feel like he doesn't want me, that he would rather with with a transsexual, AND be a transvestite.
    I just need insight. I am sorry this was so long, and probably too much information, but it's been eating at me, and he won't talk to me about it without getting nervous and saying "I don't know" to everything. I just need someone I guess "like"him to help me understand and help me accept this, because I do love him, and everything is great with him, until it comes to sex...
    Last edited by confused93; 07-24-2014 at 04:40 AM. Reason: spelling and grammar errors

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    Transgender Member Dianne S's Avatar
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    You need to talk to your boyfriend and tell him to be honest with you. If you have even the slightest doubt that he's being truthful about what he wants, what he likes, and what he feels, then IMO your relationship will fail.

    In my experience, relationship problems only get worse if they are ignored or brushed aside. It's better to confront them now while your relationship is still young and there is less at stake.

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    Happy to be me!! S. Lisa Smith's Avatar
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    Obviously we are not professionals or at least I'm not. A large number of us that are here are cross dressers. (Some are SOs of cross dressers) We are not all the same. Here is my take on what you have said. It appears that he is not really considering you in this relationship. It appears to be all him. You need to discuss this with him as Dianne has said, but my guess is that your relationship is not going to change. It is unfortunate. Good relationships are mutually beneficial. Good relationships are between equals. What you are describing does not sound like a good relationship to me. I wish I could be more positive.

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    if your having this many problems in your sex life now ,thing will only get worse. seems to be your BF has a lot of gender issues and has to be honest about it to you and himself.I was in a relationship that had a bad sex life and it never got better. You also have to be honest with yourself to see if this is all worth it . I wish you luck and keep us posted
    Roxie

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    Senior Member Read only Allison Chaynes's Avatar
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    He sounds selfish. I'd confront him honestly and tell him the relationship is not working. He must come around to your needs or you'll be miserable.

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    Gold Member Read only Rachael Leigh's Avatar
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    Word of advice, run or lay down the law and tell him a relationship is not a one person show. It takes two.
    He being 21 is very enmature as well.

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    I strongly disagree with the two preceding posts. We don't know this fella, and you seem to like him pretty well, outside the bedroom - an area that is probably very new and even intimidating to him. And honestly, no one here is in a position to offer you insights into your bf's sexuality, gender identity or the issues you've described regarding his ability to enjoy sexual relations. He probably can't himself, given his lack of prior experience. I would hope that you can persuade him to join you in seeing a counselor so that the two of you can explore what is going on in a constructive, safe environment.

    Don't run away or judge him harshly. Its a chance for both of you to grow and learn about each other.
    Last edited by kimdl93; 07-22-2014 at 09:01 PM.
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    Member Taylor Ray's Avatar
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    Young and experimental? very common.

    From a psychological standpoint, it is in your best interest to start identifying what you need in a relationship, and then seek out relationships where your needs are met.

    Are your needs being met?

    If he can't meet your needs, than i'ts just that: a process of self discovery through relationship.

    Bow to each other, wish each other well on life's journey, and thank each other for the times that you have had. Who knows, maybe you will end up best friends down the road.

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    Junior Member Betty Jean Blose's Avatar
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    Confused.....I do understand dear...been there, done that.....Taylor is correct....time to move on.....yes, always sad, but through the tears you will grow and come to realize that staying.....because you love and want to help him.....will only lead to more frustration, then suppressed anger......which must eventually burst out......

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    Little Mrs. Snarky! Nadine Spirit's Avatar
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    Hi. Welcome to the forum.

    It sounds to me as if your boyfriend is a fetish cross dresser, and not comfortable about it at all. His discomfort about it makes him unable to talk about it and accept it and work with it. It can be a tough thing for someone to come to grips with and I think it has a tendency to make some be oddly selfish in various areas.

    You sound like an incredible person who is obviously willing to put herself out there. Personally I think sexual compatability is a high priority but it takes large amounts of communication from both parties. You sound like you are doing all you can but my suggestion would be to stop any bedroom action until you two can communicate first about what is going to happen.

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    Hi there,

    As Lisa said, we are not professionals and can only provide advice based on our own experiences. I am a CDer and my wife is fully supportive of my dressing which includes going out in public. However, Isha never enters the bedroom as it would be weird for us to engage in relations with me dressed . . . so only one lovely lady in the marital bed and that is my wife. Now that is us and I am sure there are couples who integrate CDing in their relationship (in that way) and it is all 5x5 and good to go. I get from your post this is not so "for you" but is fine for him. If the act of engaging in the manner you have described is off putting for you, IMHO you need to communicate this to him and ensures he understands that what he finds enjoyable, you do not (at least that is how I read your post). Now this does not mean you have to end the relationship (if you really do like this guy) it just means that you both need to find common ground when it comes to relations in the bedroom. I agree with Kim that he is obviously trying to find his own sexuality but I also believe that you should not be a test subject if you are not desirous of such. If you have a desire to explore this avenue of your own sexuality then I recommend you discuss with him how to best approach this. On the other hand if you know in your soul this is not something for you and it never will be, then he will either have to accept you as you or as much as it might be painful, you may need to move on.

    Relationships are exciting and discovery of what you mutually enjoy are just as exciting and fun. However, if you cannot enjoy something and are only remaining because you think it is the "kind thing" to do, it will most likely take its toll on you emotionally and your relationship in time. I truly believe and open an honest discussion with him warranted. Even if he is "exploring" his sexuality, he does have to see reason as there are two people in the room and not just one.

    Hugs

    Isha
    Last edited by Marcelle; 07-22-2014 at 09:33 PM.

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    Lady By Choice Leslie Langford's Avatar
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    confused93, I read your post with great interest, and unless you're leaving out some critical relationship material here, I would not hesitate to give you the same advice that Sex and Relationship Columnist Dan Savage would likely also give in this instance. In other words:

    DTMFA: Dump The Mother-F*cker Already (used at the closing of a response in a column to indicate that immediately ending the writer's abusive or worthless relationship is advised).

    I don't know if you are familiar with Dan, but his column appears both on-line as well as in many "alternative" weekly newspapers across North America, along with some other parts of the world. He also happens to be gay, and as a result, is well versed in the types of relationship issues that members of the LGBT community often face, many of which are decidedly not "mainstream". He is also very familiar with the TG community, seems to understand what makes us tick, and generally offers both sympathetic and sound advice when one of our own reaches out to him. That said, many "straight" people turn to him for relationship advice as well, and that's not only because he doles out sound, common-sense counsel without pulling any punches, he is also very non-judgemental and has heard/seen pretty much everything at this point.

    Dan's column is entitled "Savage Love", and that is not only a play on his name, it also belies the blunt and realistic advice he offers, and which some might rightly characterize as "tough love". That said, in his world, you appear to be what he would likely define as:

    GGG: Good, Giving, and Game, which in essence means that in order to have a successful relationship, one should strive to be Good in bed, Giving "equal time and equal pleasure" to one's partner, and Game "for anything—within reason."

    You're clearly GGG, but your boyfriend appears to be a narcissistic, screwed-up case of arrested development who needs to do a whole lot of growing up (and would likely benefit from considerable professional help as well) in order to get his head screwed back on straight, and before he can successfully manage a relationship with a partner of either sex. He may be a crossdresser...maybe even a fetishistic one, but that's the least of his problems. His biggest problem is that he is an immature, selfish @sshole who will cause you endless grief over time if you allow him to drag you along on his twisted journey unless he (unlikely) mends his ways.

    Hence the Dan Savage advice of DTMFA, and the sooner you distance yourself from this needy individual who sucks the emotional energy right out of you and resolve instead to get on with your life, the better for you in the long run...

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    Senior Member KellyJameson's Avatar
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    In my opinion you cannot change someones sexuality as what they are sexually excited by. His sexuality may be unformed and undiscovered but your words leave me thinking otherwise.

    Ask yourself if he looks at you like other men have when seeing you naked. Do you see the hunger in his eyes and feel the heat of his sexual interest in you and for you?

    Often people will reject what they are naturally attracted to and try to force their sexuality to conform to what they think is the correct way of feeling and behaving. This causes misery for everyone.

    He is not rejecting you and I suspect he would be acting this way with any woman.

    Try to get him to open up about his darkest fantasies because usually that is where you find the actual persons sexuality.

    Also explore possible sexual abuse because abuse will twist the natural expression of ones sexuality as they try to resolve and make sense of the original trauma by repeating it.

    Ultimately don't compromise your own needs and wants because you will not be doing either of you any good in the long run.

    You may want to read about Crossdreamers by Jack Molay.
    The Psychology of Conformity
    https://www.youtube.com/watch?v=ARGczzoPASo

    Mars brain, Venus brain: John Gray at TEDxBend
    https://www.youtube.com/watch?v=xuM7ZS7nodk

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    Junior Member Jessy Jamz's Avatar
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    Well it sounds like your boyfriend has a crossdressing fetish and is very likely bi or gay or somewhere in the queer (in the non-gender-binary way) spectrum. He is probably confused about it and not wanting to confront it. A cding fetish means hes not really interested in sex w/o the clothes, although if he is trans or non-gender binary or whatever then of course that can be wrapped up in his sexuality as well. One thing is for certain, he's not going to magically change and just be "normal". The best thing is to see a therapist. The sooner he confronts that stuff the better, because if he keeps it hidden he's going to continue to be ashamed (which he definitely seems to be) and all that shame is really bad for your emotional health.

    He does need support so he can feel better about this stuff but don't feel like you are expected to stick with him if you have reservations about whether this is right for you. These are hard things to confront. It took way too long for me to confront my gender issues, and while my wife is supportive of me I honestly think if she knew where things would end up with our relationship she wouldn't have stuck around in the beginning. And looking at it from my perspective now I wouldn't blame her. I love her very much and value her support so so much but not being honest with myself in the past meant I was not being honest with her either...

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    hi Im sorry but he is gay , so be nice smile and say goodbye

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    Bad Influence mechamoose's Avatar
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    Hi hon. sorry for the hard time you are having.

    It sounds like your BF is having some trouble.. some with you, and some with himself.

    Gender presentation issues *really* get confused and conflated with sexuality issues. Let's get this part out of the way: He likes you, or he wouldn't be there.

    *TALK* Try and work out WHAT he likes, rather than WHO he likes.. they are not the same thing!!

    Let him know that you ACCEPT him, and he will open up enough for you to not feel insecure. (You feel insecure because you are not sure what he WANTS, right?)

    It can work, with enough trust and acceptance. I assure you that he is as lost as you are. Find your way out together!

    <3

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    Confused, take a step back and look at this relationship objectively. What does your objective self say? Occam's Razor is the only way to look at this. You can't make something happen or make someone change. Your boyfriend is confused and trying​ to be someone he is not. Be his friend but there is no future for you two. Sorry.

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    Member Cara Lacey's Avatar
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    Hi,

    First I would like to say that I enjoy many of the same videos that your boyfriend does. And I am 100% straight. I find the fantasy of watching the she males masturbate and have sex as dangerous voyage I would never take in real life.

    Second, when I first started having sex, it took me about 4 or 5 times before I had an orgasm. I was nervous! Like your boyfriend I was a late bloomer. He may come around in time.

    Third, I am in a very loving relationship with my wife and we have a very active sex life. Occasionally, I will bring my cross dressing into the bedroom. My wife does not mind, as long as I do not give her a study diet of it, which I can understand. What I rather her be excited and want me as her lesbian lover? Yes, but she just isn't wired that way.

    In any successful relationship the key is communication. Talk to him. Show him these posts. He probably isn't gay, but he is confused and trying new things. Only time will tell.

    Also remember this is his first relationship. It will take time for him to learn how to share, both physically and mentally.

    You seem to really care for this guy, so you may want to hang in there little longer and see if it works out.

    Good luck!
    Cara
    Last edited by Katey888; 07-23-2014 at 04:15 AM. Reason: TMI - explicit content deleted

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    Tell him how u feel don't allow him to where the dress all the time set some ground rules.

  20. #20
    New Member jjmetro's Avatar
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    This actually sounds somewhat similar to my friend and I. She's not my SO, only because we don't really click anywhere other than in bed. I don't dress with her, and she's not into that part. Even though I would like to be dressed, it's not just about me. Sometimes I don't "get there", but I always make sure she does as much as possible. When we first started the role reversal, I def enjoyed it, though the insecurity of someone actually willing to go there with me had its affect on me for sure. I had issues "rising to the occasion". With time this went away. I think you two need to find your boundaries, what you are and are not willing to do. insecurities fade with comfort. He also needs to know that you need satisfaction as well. You have needs as well as him. communication is the key, and if you can find some mutual ground, I'm sure you can have some mind blowing sex. If you've incorporated this much, this early, there's only the limits you set. For someone with unusual tastes (him), finding a willing, even though unsure, partner (you) is a godsend. Remind him that he is lucky to find someone that is willing to cater to his fetish, but that you also need him to reciprocate.

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    So you joined 2 weeks ago and are 21 and presumably a female? Have you read the how straight of a guy are you thread?

    Your entire post gives every indication that your fella is "turned on" by many things...

    but YOU are not one of them. At his age, the chances of you changing that are probably slim and none.

    But IF all his other qualities make him a "keeper" you can try.

  22. #22
    Female Illusionist! docrobbysherry's Avatar
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    I am a single, straight fetish dresser, Confused. I've been dealing with this issue for about 17 years and I'm 70 now. I find the sex to be good and very addicting. I'm not attracted to men no matter how they're dressed. And, I'm having difficulty finding "room" in my life for a female partner. But, that is just me and may have nothing to do with your BF.

    Here is my opinion, tho. U r both too young to form a life partnership that will last. At 21, most men with no gender issues don't know S from Shinola. He may be telling u the truth when he says he doesn't know. And, may be trying to figure himself out for many, many years. As I am.

    When u 2 break up, u will look back on this relationship as a learning experience. As it should be. Fortunately for u, and probably unfortunately for him. U will eventually find someone who appreciates u. While he may look back on u as the special one he drove away!
    Last edited by docrobbysherry; 07-23-2014 at 12:17 AM.
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  23. #23
    Senior Member Amanda M's Avatar
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    Looks as if your man is in a very confused state. What is clear is that he is moresexually attracted to his various fetishes than he is to you. That is the bottom line. Now you MAY be able to help him change, but frankly, it is unlikely that you will succed. Answer this simple question - is the way his sexuality presents a good foundation for a loving and fulfilling relationship for you? Only you can answer that. When you have done, honestly, bearing in mind all YOUR needs, wants and hopes for the future, you will knowwhat to do.
    If you always do what you always did, you'll always get what you always got!

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    @Confused93 - You have some information about your SO now, but you don't really know enough yet to make an informed decision, in my opinion. I would ask though, whether or not the relationship is really good in every way except for sex, and perhaps for your discomfort over his crossdressing? The reason I ask is that by all appearances, you are a straight girl, and he appears to be a crossdresser, at the very least. That is not the easiest combination for a relationship. It can certainly work out OK, but it's not for everyone.

    By the way, I suspect your SO's attraction to transgender pornography is WAY more common amongst crossdressers and other transgender MtF's. Not many on this forum will likely admit that they like this stuff too - I certainly did back before I understood my own gender issues. (I hate this stuff like poison, now. It is totally degrading.) Anyway, that's not as rare as you might think.

    So I'll talk about one of your sex issues first - namely that you make him orgasm, and then he does nothing for you. The way around this is to have sex more the way lesbians have it - take turns making one another feel good. Since he has neglected you, I'd make him start, and then only do what he likes once you've climaxed. (I'm a lesbian, and yeah, we tend to take turns with each other.) This brings up a few things that may make this difficult for you:
    1. He seems to have difficulties with penetrative sex - this may be a big problem for you, as many straight women prefer this to anything else
    2. YOU may not be very comfortable with your own sexuality / sex role - when you have sex with him CDed, with you as the top, and you penetrating HIM. These are stumbling blocks for a lot of women - and I believe you mentioned that doing these things were not great for you.
    3. You may find that alternating making one another feel good isn't as satisfying for you - climaxing together is sort of the holy grail for many straight people.
    4. You both seem like you are "bottoms" sexually. This isn't an impossible situation, but you both may really have difficulty feeling fulfilled sexually because both of you seem to need your partner to "take charge."

    I would also ask your SO to tell you his whole history of crossdressing, and his interest in transgender women. When did he start CDing? Does he want to completely present as a woman sometime, or is just wearing a garment or two all he cares about. Would he want to be crossdressed at other times, other than sex? Don't be judgmental about this stuff, or at least try not to be. I'm sure it all seems pretty weird to you. (BTW, his desire for anal sex doesn't mean he's gay - this is more common in straight men than you might expect.) It'll be hard for him to talk about this stuff, in all likelihood.

    I hope you are both able to be happy together, if that's what's meant to be, and that it isn't, you can break it off amicably and before either of you are totally invested in the relationship. Be prepared to consider a little counseling as a couple with a therapist who understands sex / gender issues.


    @The Forum - By the way, it's really reassuring that seemingly so many on this forum view the young man's attraction to transgender women as a fetish - as if someone can't be legitimately attracted to us for our own innate qualities as human beings. Thanks - I feel really validated as a person now! I mean, sure, the pornography he likes is quite unrealistic as is most pornography, but I'd hoped that folks on the forum here would view women such as me as people, rather than as objects for a paraphiliac's sexual gratification. (But what the hell, the rest of the world mostly views us that way anyway, so what am I complaining about?)

  25. #25
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    Quote Originally Posted by KellyJameson View Post

    Ask yourself if he looks at you like other men have when seeing you naked. Do you see the hunger in his eyes and feel the heat of his sexual interest in you and for you?

    Often people will reject what they are naturally attracted to and try to force their sexuality to conform to what they think is the correct way of feeling and behaving. This causes misery for everyone.

    He is not rejecting you and I suspect he would be acting this way with any woman.
    .
    Yep, I have lived this for many years. It took my H finally acknowledging he IS a fetish dresser for me to finally understand all this. Sometimes, and I assume this is out of shame or perhaps social pressure, crossdressers will say it's about 'feminine expression' when really they mean 'sexual expression'. I'd suspected this for years as my H's behavior never added up to what he told me. Counselling, major marital upheaval and time finally revealed the truth. Now, it all makes sense and yes, he does look at me differently than a 'normal' heterosexual man. His desire for me will always be tempered by his desire for his fetish.

    I don't know what the other side of this is like, living with a trans dresser, but I can say the fetish dresser has major difficulties in a relationship, too. I agree with Leslie that Dan Savage is the go to guru here, and I also agree you've done your bit. You're young. You have time!

    If your profile name reflects your birth year, go have fun and forget this heavy nonsense. You only get a twenty one year old's body once. What I would do with it if I had it back!
    Last edited by Tinkerbell-GG; 07-23-2014 at 04:19 AM.

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