Recently married and having difficulties

I'm 26, Male, recently got married to the love of my life.

Before my wife, I had sex with 3 other women with mostly good results. I was an attentive lover and my partner's pleasure always took the forefront in my mind.

My wife is transgender and that means her dick is the first I have ever interacted with. Turns out I love it. Way more than pussy. I'm not sure what it is about it, but it's just the right fit for me. I love to touch it and suck it.

She is very understanding of my obsession with her dick and she lets me do whatever I want with it. Obviously she also enjoys that. Because of her hormones, it takes a very long time for her to cum and sometimes it just doesn't happen at all. I understand that this is a normal side effect of her treatment, but I do often feel a sense of failure for not making her cum. When she does cum, however, it's amazing. One of the best feelings in the world.

She is also very good at giving blow jobs despite being a complete virgin before our relationship. She sucks my dick with the perfect speed and suction that I'll sometimes cum in under a minute, which she loves.

The point I'm trying to make is that oral sex in our marriage is excellent. Neither of us have any concerns about that. Our only really problem is anal sex.

Her dick is a little small, which I find very cute and attractive, but when she tries to fuck me, she can't cum. She just can't get deep enough to feel anything good. And my dick is, shall we say... bigger than average. She's a very small woman and that applies to her butthole. She's extremely tight.

Despite trying many times, we haven't had any success with anal sex in the two years we've been trying. No amount of lube will help. Believe me, we've tried different formulas, even buying those injectors so she has lube all the way up her ass. But she can barely fit my finger. Plus she says it's very painful to even do that.

She hasn't experienced the pleasure of a prostate orgasm. I have, because I experimented with toys when i was younger. But her first toys were the butt plugs I bought her as part of an anal stretching set. The type where there are three butt plugs of increasing size, plus one full size dildo to get used to a dick. The dildo is almost as big as me, so we figured if she can fit that, it'll only be a little jump to the real thing.

Well... she can fit the smallest butt plug. But every single time she tries to use the next size up there is no luck whatsoever. She complains of tight pain in her butt and losing all desire to try.

We both really want to improve this part of our sex life and I'm hoping that someone here might have some tips. Do we just persevere through her pain? Are we doing something wrong?

 

Try oral on her first , getting her going work her anal massage it for awhile with a some lube around it , do that while you are both 69 each other .when I use a toy on me I have to lubed and so into it !!

 

What a fabulous way to "introduce yourself".

 

Thank you! Pm if you want

 

Have you tried poppers at all?

 

A couple of comments for this thread. One is that your wife has difficulty due to hormone therapy cumming from oral. The same will apply as she is penetrating your anus with her cock. The anti-androgens from HRT reduces testicle size, slows erection frequency, and impedes sex drive. This causes the trans person to have a harder time reaching orgasm and ejaculation but does not affect the want to be intimate with a partner. She will still love you holding and cuddling her and reward you with those fabulous blow jobs. The second is that some people, myself included, cannot accept large objects in their anal cavity. I used to but age and other complications prevent me from enjoying large objects penetrating me anymore. No matter how much one tries the stretching of the anal opening and rectum can be painful. It may be possible over time to get her to be able to accept your cock without discomfort but it may take a lot of patience and perseverance to get there. I suggest you look for an even smaller anal toy and take more time in working her up to it. What you don't want to do is force the issue and damage the anal cavity. You could also look into surgery, or at least a medical exam, to determine there isn't something amiss with her rectal tract. Hope this helps but most important is for you to love her as she is.

 

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