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

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  1. #1
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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

  2. #2
    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.

  3. #3
    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.

  4. #4
    New Member flutterby's Avatar
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    While I do not consider myself a fetish dresser, and do take some offense at the negative connotations being associated with trasngender porn and those who enjoy it, I can assure you it is possible to have a healthy sexual relationship with the RIGHT person, regardless of the situation. Notice I said the RIGHT person. I am very attracted to my wife and she me, regardless of what I am wearing, what position we are in, or who is doing the penetrating. We are right for one another, but I am not so sure about you and your BF. You should sit him down and tell him how you feel, if you two can then be honest with yourselves and each other, you may be able to decide if your relationship is worth saving or not.

    And no the desire for anal sex does not make you gay, but my wife and I do make very good lipstick lesbians. lol

  5. #5
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    I'm really saddened to see so many in the community here so ready to throw the young man under the bus.

  6. #6
    Worlds Prettiest Dad!!! Jocelyn Quivers's Avatar
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    I'm another one who feels the boyfriend is very harshly being dogged, thrown under the bus etc. If in addition to everything you listed your boyfriend physically and emotionally abused you, used, Crystal Meth, Heroine, Crack, abused alcohol, had multiple kids with other women, cheated on you with another person. Sure break up with him now, and move on.

    I'm going to assume he does not do any of those things listed, so please try and give him time to figure out and accept who he is. Self acceptance especially at 21 is a very hard thing for anyone. I'm almost 40 and I'm still having my own acceptance issues about where I actually am on the TG spectrum. So pleased be prepared to read through drawn out tale of my life during my life at 21. At 21 I believed I was not trans and lived life with belief of my sole purpose in life was to defeat this unholy monster inside of me which was my femme side by any means necessary. That meant being going into a completely male dominated, considered masculine occupation, lift weights, shave my head, have a big bushy mustache etc. I also was under the misbelief, that because I was still a virgin at 21 (not by choice either) that once I found a GG this god-awful side of me would be eliminated. Well once I met a wonderful GG at that time, my grand plan of girlfriend = no more cross dressing/etc did not go as planned. To my own horror what existed for a femme side at that time started becoming stronger. Yes I loved the woman I was dating at the time with a passion, but was still very confused/not accepting the person I actually was because this could not be. I was a GM, I now had the attractive GG friend, was supposed to start thinking about marriage, go to the top of my profession. Why dear God am is this other side of me not going away, and actually becoming stronger. Of course this started making me more irritable and more of a jerk to in the process. Long story short girlfriend had enough, broke up with me, I had to finally accept the fact that I might have wanted to be all 100% male but that was not the person I am, and I started down the path of accepting my femme side and allowing that side to grow to wear I'm at now.

    So I will take a guess that your boyfriend is going through similar issues of trying to come terms with who he is. Continue to be patient and understanding, but also lay down a few rules about your needs, concerns etc.
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    Quote Originally Posted by tammie View Post
    hi Im sorry but he is gay , so be nice smile and say goodbye
    NEWSFLASH: Gay men are not into (MTF) transsexuals or transsexual porn (also MTF obviously), because they're attracted to men or masculinity. Given the abundance of transsexual porn, it's a safe bet to say it's more of a heterosexual thing, if not typically heterosexual.

    Quote Originally Posted by PaulaQ View Post
    I'm really saddened to see so many in the community here so ready to throw the young man under the bus.
    THIS. This thread is unbelievably judgmental. Topic starter, you didn't really ask for advice in the first place but got loads of it anyway. One piece of advice from me anyway: be careful with 'advice' from complete strangers who don't have any stake in the outcome. Free advice is worth what you pay for it.

  8. #8
    Aspiring Member Jenny Elwood's Avatar
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    Hi Confused?

    I don't have the time nor the inclination to read through all the posts, so I'll just respond to the original post. Maybe my post will just confuse you further, or maybe it will give you some insight, take it as you like.

    I identify a lot of myself in your BF when I was that age (from what I can tell you are still young adults?). Crossdressing at the time was still very sexual for me as well. I identified myself as heterosexual but very unsuccessful at it! By the time I met my wife (approaching 30) I had only been with one girl twice. Since getting married I have ALWAYS suffered from the fear of not being able to perform as a man, despite the fact that I have five kids to proof the contrary. But, though I'm sure my wife may have longings for a wilder sex life, I try to live up to my end of the bargain. Jenny stays out of the bedroom and I'm working on keeping Jenny out of my head at those times as well.

    What I'm trying to say is this: This thing really can go either way and it's all up to your boyfriend and the choices he makes that will define his life and/or your life together. He has to make the decision where he wants to go with this thing, and I can only hope for your sake that he is truthful about it to you. Though most of us have no say in the matter of being a crossdresser, we can excercise some measure of control over it and still make good life affecting decisions. I choose my wife and the life I have with her, crosdressing comes second.
    Last edited by Jenny Elwood; 08-02-2014 at 03:04 AM.

  9. #9
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    This is a no brainer. He's a loser & you deserve much better. Dump the bum!!!

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    New Member Kylee-Blackstad's Avatar
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    I remember being 18-years-old myself with my first serious partner and all of it's awkwardness. As others have said the issue really isn't so much as the cross dressing in an of itself, but your boyfriends awkward inexperience with everything alongside various embarrassing kinks you are probably not going to like. Had he been able to articulate and know his sexual limitations and communicate them in a mature way to you, it may have turned out somewhat better. But he's obviously not confident enough to do so.

    Quote Originally Posted by confused93
    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.
    So he's into hentai especially of the futanari persuasion. I'm not surprised from what you've written. The fact he's got porn on his phone certainly suggests to me a certain issue. I know from around the block a lot of couples have intimacy issues when most of their one partner's focus is on a specific kind of porn. My gut tells me he might have performance anxiety having had no prior sexual experience. I certainly did with my first partner.

    You've only been dating 7 months. It's kind of a whoop de do time frame in my book. His inexperience with relationships didn't tell him it's a good idea to be upfront about kinks, because they can be deal breakers for some people. As hard as they can be to disclose. If his kink needs are too uncomfortable for you, it would be best to leave.

    If you wish to stay with him, it sounds like you both need to have a very long and candid chat about sex and kink in a very non-judgmental way. You yourself should probably think hard to whether it's worth all that work.
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  11. #11
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    all men have a female side. most are scared to show it because they feel its a weak side of them. you have to figure out on York own if yo want a man like him. do u love him? my wife does my makeup for me. she tells what dresses i look good in. Im not saying he's like me it could just be a phase. but if it's not can u handle it and do u want to? trust your heart it will Leeds u! my best wishes for u

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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

  13. #13
    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.

  14. #14
    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...

  15. #15
    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.

  16. #16
    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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  17. #17
    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

  18. #18
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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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  19. #19
    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.

  20. #20
    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.

  21. #21
    GG ReineD's Avatar
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    Quote Originally Posted by Nadine Spirit View Post
    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.
    I agree with Nadine. Your boyfriend was able to come to completion when he wore the dress (he only has that one dress?) and at this point, it is obviously not about crossdressing all the way to present as a female. Your boyfriend may perhaps be accustomed to getting off when solo with the help of trannie-porn and it may be difficult for him to transfer his sexual energies to you.

    This is not all that different than any guy who becomes used to getting off on any type of porn, to the degree that he has difficulties with completion with a real female partner. This is actually a rather common and growing issue:

    http://www.psychologytoday.com/blog/...-contribute-ed

    If you're interested in a more scientific explanation, follow the links in the link below:

    http://www.yourbrainrebalanced.com/index.php?topic=2.0

    I'm sure that your boyfriend does want to be sexual with you and it is no doubt distressing for him to be reacting this way. I suggest you both become thoroughly familiar with the articles I've posted above. You can take what you feel fits your circumstances and leave the rest. And as was suggested earlier, perhaps find a sex therapist who can help.

    Here is an account of a 28 year old who got beyond this. Granted his fetish wasn't CD-related and the extent that he watched porn might be extreme, but honestly I believe the principles are the same:

    http://yourbrainonporn.com/book/export/html/490

    On a last note, many people in this forum have moved beyond the sexual aspect of the crossdressing and they now dress for reasons of comfort or for identity reasons, even if they are not transsexual. They may be quick to point out that your boyfriend may also have it in him to eventually want to present fully as a woman and experience femininity. But even if he does, he will still need to move beyond the stage he is in right now, and separate the crossdressing from it's purely sexual nature. This obviously is especially important if he wishes to have any intimacy of a sexual nature with you.
    Reine

  22. #22
    Bad Influence mechamoose's Avatar
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    Quote Originally Posted by ReineD View Post
    On a last note, many people in this forum have moved beyond the sexual aspect of the crossdressing and they now dress for reasons of comfort or for identity reasons, even if they are not transsexual. They may be quick to point out that your boyfriend may also have it in him to eventually want to present fully as a woman and experience femininity. But even if he does, he will still need to move beyond the stage he is in right now, and separate the crossdressing from it's purely sexual nature. This obviously is especially important if he wishes to have any intimacy of a sexual nature with you.
    You guys are young, you are still figuring out who you are inside.

    I'd suggest that because you love each other, try and remember that you are both still figuring things out, and you don't really know the way or the method to becoming who you will eventually be. Allow yourselves the room to explore who you are... Sometimes you will take bad paths, but mistakes happen.

    Just remember who you are to each other, and at the end of the day that you will be sleeping next to each other.

    Good luck you two!!

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  23. #23
    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......

  24. #24
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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.

  25. #25
    Senior Member KellyJameson's Avatar
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    Aug 2011
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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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