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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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    Jul 2014
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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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