I have no idea what I am doing or what to do.

[HarryWest]

I have no idea what I am doing or what to do.
I was attracted to a girl who turned out to be (and I'm not sure if I'm using the correct terminology and Dr. Google was very confusing for me with it all) a non-operative Male-to-Female Transgender.
That didn't seem to worry me much when she first told me and explained her situation. We have been dating for about seven months now.
However the other day for the first time in our relationship things got a bit more heated than just kissing and a bit of petting. And I realised, and this is going to come off wrong, but I mean as in I actually realised that she wasn't like all the other girls I have been with in the past.
And so we had another little conversation about how she was still quite functional and got sexual release the same way I did and wanted me tomake love to her and she wanted to  me.
I was confused, out of place and just a bit intimidated. I mean I like her a lot and we've always had a relationship where's she's been the one to lead and me to follow.
That's what really attracted me to her was her ability to just push forward and strive for the best. It never occurred to me (and I'm stupid for not really thinking about it sooner) that she was not exactly... a she.
I just don't know what to do.



Don't use foul language on this site - or to her!
https://www.susans.org/forums/index.php/topic,159177.0.html

[Kyra553]

Love her the same way you have for the past seven months. Some things will be different then a cis relationship. But hardly any of those differences are a disadvantage or something to be ashamed of. You were attracted to her and stayed with her this long. Why feel confused now when nothing has changed?

Welcome to Susan's forum ^_^

[AnneB]

Harry,
Kira said the same thing I think we all would say.  Do you love her?  Tell her, and you will figure it out together.  Yes, it will mess with your head, it will be confusing, but if you really love her, it wont matter anymore.

[HarryWest]

I guess I'm just hung up on the physicality of it. Which is very male-male to me, whereas the strong emotional connection we have has only ever been male-female.
I like her a lot; I love her on many levels.  Can that be said in a mutually exclusive way... maybe not, but it is how I feel. I love her, I care for her, I sure as hell don't want to hurt her or lose her and I'm scared.
We are compatible in our lives and links. We have shared some very emotional moments together and I have always been emotionally and sexually attracted to her.  Nothing has changed?
All the above I have said to her and more.
But I have never done anything like this before... in this way not even with (to put it correctly) an actual biological woman let alone had something like this done to me, with me or for me. I admit I'm not repulsed by the idea, just not (and for me this is the correct expression) 'understanding' of it.
It has just got so confusing all of a sudden.

[Carlota]

Taking it slow is probably the best thing I can tell you. If she is your first, con más ganas (better yet). To be honest, rushing into it isn't your best option. If ya'll care about each other, take things slow. You don't have to do A - Z in one day, even in one month. That's the beauty of being with someone you love, things will happen when you both are ready. Not when you're ready, or she's ready. BOTH of you have to be ready. If you're confused, or lost, hold your horses cowboy (sorry, two years in Texas has changed me significantly). Communication with her is so important. I know there were things that were new to me when I started off with Sarah. Stuff health class never covered. To top it off, I was a super virgin (not even a kiss on the lips from another person). But talking to her helped me out. Heck, there are still times when intimacy gets wacky, but we gotta stop, rewind, and dissect it. If I missed the point, just redirect me, lol.

Another thing, trust is super important. And what is a great way to build trust, well time and communication! 😀

God, I talk to much. Lol.

[sad panda]

What bothers you about it? I mean, what is making you hesitate? You say you're hung up but.. I mean, have you asked yourself why you are feeling this way, beyond just the physical dynamic?

You don't have to want it, but, also, there's no reason to not explore what works for you just because of some principal or I guess a fear?

Y'know, either way, if you want it you want it, if you don't you don't. 🙂

[Jessica Merriman]

Love her the same way you have for the past seven months. Some things will be different then a cis relationship. But hardly any of those differences are a disadvantage or something to be ashamed of. You were attracted to her and stayed with her this long. Why feel confused now when nothing has changed?

Welcome to Susan's forum ^_^

Definitely this /\. She is a female, just different physically. It is the person you fell in love with and want to be around. Don't let pre conceived notions or societies views destroy what you have with her. Take it slow if it is more comfortable, but don't distance yourself from her based on physical features. She is all woman!  🙂

[HarryWest]

Thank-you all for your input. Just talking to someone in this manner is very reassuring and while I do talk with Jess about these things I just get so embarrassed and nervous.
All my relationships I have been attracted to strong dominant women. Women who like to be on top, I mean not BDSM level just forceful and aggressive not controlling.
But last night Jess came over to my flat and we talked, or accurately she answered my questions.
Then she took me into my bedroom and introduced me to her body. I have seen her naked in the past, like when we had to dry off after a rainstorm or the couple of times we went skinny dipping in the dam on her parents' farm. It never bothered me.
She undressed down to her bra and panties to show me everything, explained the different surgeries and augmentations she has had done, what all the little cuts and scars meant.
And she did this all in a rather sexy sultry way that really turned me on, and while I'm writing this it feels like I'm writing softcore porn, but then she removed her very lacy underwear and introduced me to her penis.
She told me nothing needed to happen that night and all this was about getting to know you and such but I felt two very conflicting emotions right then and there.
I still felt the super sexual attraction that said take her, "make love to her" and make her yours but I also had the same feeling I used to have in the school locker room when I just wanted to run and hide when the more developed older boys came into the shower room.
She's hot, she's gorgeous, she's stunning, she's beautiful. I'm emotionally involved and physically attracted but sexually scared. She makes me feel special and always been one to guide me and help. I trust her nigh unconditionally.
I'm receptive and willing I just don't feel able. Does that make sense?

[AnneB]

It does make sense, just keep in your mind, and in your heart, you are not in a race, there is no schedule of events, no timetable that says you have to do this and this and this, now, and in ten minutes, in two hours.. you don't have to do anything.  You and Jess set the timetable, together. When you want to, when each of you are ready, comfortable.

Locker room feelings will be there.  Its part of your life. Your memories, but your heart will find a way to change that feeling.  Love will help.

[HarryWest]

Ok.

We have been doing the whole touchy feel me up stuff for the whole month thereabouts and we have become comfortable with that.

Oral has kinda gone ok too, both ways me and her.

We have not gotten anywhere near penetrative sex yet and I'm really here to ask how to go about it?

Never done this before and while Jess is rather knowledgeable I don't want to be caught unprepared for that eventuality.

[Juliett]

Astroglide lube and take it very slow and very gentle. It make take a few tries depending on how experienced she is. I know there is no greater feeling in the world than when my bf grabs my hips from behind and gives it to me good.

[AnneB]

Oh my...   I'm feeling faint!!    😛

[HarryWest]

Well I'm really out of place now, never gone shopping for lube before, more a Vitamin E sort of guy.

Jess said we are going to try something special next week and two things come to my mind...

Firstly, condoms? I'm pretty sure I don't have anything in her size and since Jess has never brought any over, I want to have a pack on hand. Is there a better type for anal play?

Secondly. I'm more concerned with Jess having sex with me than me having sex with Jess. Jess has heavily shown her desire. Teasing/playing with me while performing oral etc. I am interested and accepting but I feel unprepared.

[HarryWest]

Jess and I tried anal sex (with me) for the first time last night.

She fingered me and toyed around for a while and when I felt I was ready, we went for it.

It was at times quite painful and overall it felt very uncomfortable for me, but at first it felt quite nice in a weird and deeply personal way that I just cannot put to words.

Had to stop quite a lot and eventually we just kind of gave up because I just couldn't take any more.

We used a really good silicone based lube and reapplied the stuff frequently.

Jess was disappointed and I felt sort of bad (and not in just the physical sense) as we had no trouble the other way around.

Does anyone have any advice for me to help get myself to a point where this will be bearable?

I really wanted to enjoy it, but I couldn't fully and I'm scared that next time we try, the memory of the first time might make things even worse?

[StraightInLoveMTF]

I think it's wonderful that you are being openminded and willing to try new and different things. I too am getting ready to experiment with some new things with my MTF partner. She went last week and bought us a strap on. We were suppose to last night but ended up not which I was kinda disappointed but yet been so nervous. I have had fantasies of being a male and having sex with a female (many many times) but always been just a fantasy. Now one of fantasies will become reality. I just hope I can satisfy her and not be emotional if it doesn't as well as I want.

So I guess my post is to tell you that I think its wonderful you didn't bail on Jess first off when Jess shared with you. When my girl told me and the first few times I saw her as a her I was taken back a little because the person I was led on to love was so rough tough manly men of them all to find out that was her outter most shell she wore to those who didn't know the real her because people can be such judgemental ->-bleeped-<-s. But I knew how much I loved her and how I felt when I didn't see her that I didn't love her because she was a male and has a cock. I fell in love with her for so many other things....her heart, her mind, how she treated me and my kids, her toughness, etc....

And second off that you are openminded like me. I want to please my girl....she takes very good care of me.....much better than I have ever had so if there is something she wants then hell yeah. Just wish I had more experience with this stuff so I could have confidence. But that will come with practice

Best wishes for you and Jess. 

[Kyra553]

Jess and I tried anal sex (with me) for the first time last night.

She fingered me and toyed around for a while and when I felt I was ready, we went for it.

It was at times quite painful and overall it felt very uncomfortable for me, but at first it felt quite nice in a weird and deeply personal way that I just cannot put to words.

Had to stop quite a lot and eventually we just kind of gave up because I just couldn't take any more.

We used a really good silicone based lube and reapplied the stuff frequently.

Jess was disappointed and I felt sort of bad (and not in just the physical sense) as we had no trouble the other way around.

Does anyone have any advice for me to help get myself to a point where this will be bearable?

I really wanted to enjoy it, but I couldn't fully and I'm scared that next time we try, the memory of the first time might make things even worse?

Lovin the updates, keep them coming!! =)

Hmm rear end fun for the first time.... Best advice I have is that it takes much much practice before you enjoy anal play. It's a new thing for your bum so give it time to stretch and heal. Then you to will learn how wonderful prostage orgasams are! (I highly recommend it hehe) If you want to help yourself adjust faster (but more painful) invest in a small butt plug and gauge up from there when your ready. 

It's also great to hear you've become more understanding and accepting of her. Those two things will mean the world to her so never lose them, now that you've found them. =)

Love reading your posts!

[HarryWest]

Lovin the updates, keep them coming!! =)

Hmm rear end fun for the first time.... Best advice I have is that it takes much much practice before you enjoy anal play. It's a new thing for your bum so give it time to stretch and heal. Then you to will learn how wonderful prostage orgasams are! (I highly recommend it hehe) If you want to help yourself adjust faster (but more painful) invest in a small butt plug and gauge up from there when your ready. 

It's also great to hear you've become more understanding and accepting of her. Those two things will mean the world to her so never lose them, now that you've found them. =)

Love reading your posts!

Well we went for round two yesterday.

Jess is more experienced in many ways than I am and I trust her deeply but she is a lot bigger than me and it's off putting on it's own.

She brought over some toys and teased me wider than before.

I felt more comfortable knowing what was going to happen but I was very tense which I guess didn't help and things ended quickly.

Jess was understanding but she really wanted to get off, but after all the attention put into preparing me, I was really tired (and not in the mood anymore).

I'm really new to this. Advice?

[Kyra553]

Well we went for round two yesterday.

Jess is more experienced in many ways than I am and I trust her deeply but she is a lot bigger than me and it's off putting on it's own.

She brought over some toys and teased me wider than before.

I felt more comfortable knowing what was going to happen but I was very tense which I guess didn't help and things ended quickly.

Jess was understanding but she really wanted to get off, but after all the attention put into preparing me, I was really tired (and not in the mood anymore).

I'm really new to this. Advice?

Just know that you gotta stay in and you gotta think it's a good experience. I would say start with her next time and hold off until she has climaxed. She will stay in until you finish I'm sure.

Oh...when it's in .. try to shake your hips . Nothing feels better than that I assure you. =)

[HarryWest]

Just know that you gotta stay in and you gotta think it's a good experience. I would say start with her next time and hold off until she has climaxed. She will stay in until you finish I'm sure.

Oh...when it's in .. try to shake your hips . Nothing feels better than that I assure you. =)

I'm still not sure I am getting used to it. I think the situation Jess is looking for is... Jess wants to reach penetrative release inside me. I just cannot handle her, she just feels so uncomfortably big inside me.

I took a huge step out of my comfort zone and went out and brought a set of three trainers(?) from the local adult shop. The manager was very helpful and she gave me what I hope is good and correct advice.

She said when her partner wanted to try anal with her it was a slow and laborious progression from teasing to toys to taking. I find the smallest size quite comfortable and easy to accept the middle size provides some pressure but is nothing like Jess. I'm kind of nervous about the largest which is very bulbous.

I'm still not at all sure about condoms as the ones we are using keep ripping, tearing or rolling off completely.

[Alice Rogers]

Hun, one word. RELAX. Anal sex is totally dependent on the person on the receiving end being relaxed and calm, when you are stressed you will subconsciously tighten up, no amount of anal training with fingers and plugs will help if you don't relax the muscle involved, I know from experience what it feels like to have a partner with a large penis and yes, it takes a little more getting used to, but It's not about stretching yourself its about accepting it and letting that muscle untense.

My boyfriend is very well endowed and with a little careful start I now wouldn't want him any other way.

(silly thing to say here but also there will be no permanent damage to your muscle back there if you are relaxed, it's just like any other muscle, it recovers!)