So here I am, in unfamiliar territory...

[Feral_Sophisticate]

My girlfriend - as we've discovered via time and experience, together - is demisexual. She and I have been kinky from the get-go, which is how we began, really.

There have been some sexual things that have interested her, and we've explored some of them - purely on her own initiative. Due to some prior incidents with abusive relationships with older men, the fact that I haven't been operating on my own agenda, and that I've had zero expectations (or a sense of entitlement), she's become more comfortable within her own asexuality.

Prior to meeting her, I'd had a variety of unsatisfying interactions with members of the opposite sex, which lead me to deciding to take sex off the table for future interactions with the women I met in the world, and instead work on developing real relationships. In her, I found one.

So, fast forward to today. She's curious to explore other things that were previously on her "not interested in, and not gonna happen" list. I know a large degree of that is because she's with someone that she trusts to be good with her boundaries. We're at the point where she's told me that she wants me to be the one to "punch her v-card". Given that I've been abstinent for over a year, and that I'm looking upon this as a "fresh start" (as my first time was memorable, but not in a positive light), this is really going to be a "first time" for us both - and she sees it as such, too.

Here's the kicker - she's actually kind of excited about our upcoming "special date night". I'm intending to make it just that, a very special night for us both, where we'll play as we often do (as far as the kinky stuff is concerned), but with taking things one step further. I'm beyond flattered, as I love her dearly.

I want her first time to be special, memorable and something wonderful for us both to share. She has a mild degree of vaginismus, but we have managed penetrative play before (obviously, not PIV penetration), and it's not been as difficult as she was afraid it might be.

So, my questions are thus:

Has anyone else here had their "first time" with the person they're currently with...? How did it go? (and no, I don't need the "how to", as I'm quite familiar with how the pieces fit together)

In particular, if you're the sexual side of the relationship, I'd like to hear your side of the story...

Thanks. :)

[argar]

I haven't ever had a "first time," but I do have a few observations.

I think its important you have a sense of humor about your time together. Tell each other jokes, laugh, relax with each other. Don't make it a night that is so serious all you have is tension. True intimacy, in my opinion, isn't necessarily about who got an orgasm, but the time you guys spend together, that special time together is intimacy. Heck one of the intimate things I would love to try with my special someone is playing that game were you write letters in each others back and try to guess what it is.

That's all I got, yes sex, but every before and after is what makes it special in my opinion.

Have a beautiful night.

[Wyrmcraft]

I agree with Argar. I have had a few very intimate moments with my ex but we never got quite the full way. Still, I wouldn't trade those memories for anything. A lot of what will make the night are the fantastic memories, and there is a lot more than just the main event. Try to make the whole night special, and if she is a romantic (because I am a hopeless romantic at heart) you can really make things special just by knowing what she wants and likes. Be yourself, but try to make her feel like she is special and loved, and pull out all the stops on making it special. I know the old rose petals on the bed is a terrible cliche but some people appreciate it, I would if my gender was reversed.

It really depends on what you two are like as people though, you know each other better than anyone else, just do what feels right and I am sure you two will have a wonderful night.

There is this certain thrill to learning all about someone else's body, and while you two are quite familiar to each other, just remember that the basics of BDSM travel well into sex as well. Establish comfort zones, have a safe word, and listen to each other about what feels good. Try to make her feel comfortable and calm. While I'd personally play the night up as romantic myself (again, hopeless romantic) I would also make sure there wasn't too much excitement. Her being stressed or being all tight from excitement will make it worse, at least that is what I have been lead to understand. Try to make her comfortable, and perhaps blend in a few of the tricks you've learned from knowing her body the way you do. If there is something that calms her down or luls her out, apply that as necessary, and if you feel you need a little bit more excitement do whatever makes her excited whether it is earlobe nibbling for massaging her feet.

Basically, just react to her, and have her react to you based on what you know of each other, and you will have a wonderful night.

I miss my Ex, a lot.

Good luck Feral.

[Feral_Sophisticate]

I think its important you have a sense of humor about your time together. Tell each other jokes, laugh, relax with each other. Don't make it a night that is so serious all you have is tension. True intimacy, in my opinion, isn't necessarily about who got an orgasm, but the time you guys spend together, that special time together is intimacy. Heck one of the intimate things I would love to try with my special someone is playing that game were you write letters in each others back and try to guess what it is.

Have a beautiful night.

I don't think having a sense of humour will be a challenge. We already have a lot of that - in and out of the bedroom (as well as her in and out of bondage), so that's already a given. My intention is that it'll just be a date night, just one that will be a bit more special than most, and where our kink play will just evolve past boundaries where neither of us had thread together before. Obviously, if she has second thoughts along the way, it's full stop for me, as I'll have it no other way.

And I fully get what you say about intimacy, as that's really where we're at. We do the drawing on each other's bodies with our fingers (and guessing what's being written). We cuddle a lot, hold hands in public and do little things to help each other out - often without being asked to do so.

I think it will be a beautiful night, too - and in many ways, it will be my first time, too.

I agree with Argar. I have had a few very intimate moments with my ex but we never got quite the full way. Still, I wouldn't trade those memories for anything. A lot of what will make the night are the fantastic memories, and there is a lot more than just the main event. Try to make the whole night special, and if she is a romantic (because I am a hopeless romantic at heart) you can really make things special just by knowing what she wants and likes. Be yourself, but try to make her feel like she is special and loved, and pull out all the stops on making it special. I know the old rose petals on the bed is a terrible cliche but some people appreciate it, I would if my gender was reversed.

It really depends on what you two are like as people though, you know each other better than anyone else, just do what feels right and I am sure you two will have a wonderful night.

There is this certain thrill to learning all about someone else's body, and while you two are quite familiar to each other, just remember that the basics of BDSM travel well into sex as well. Establish comfort zones, have a safe word, and listen to each other about what feels good. Try to make her feel comfortable and calm. While I'd personally play the night up as romantic myself (again, hopeless romantic) I would also make sure there wasn't too much excitement. Her being stressed or being all tight from excitement will make it worse, at least that is what I have been lead to understand. Try to make her comfortable, and perhaps blend in a few of the tricks you've learned from knowing her body the way you do. If there is something that calms her down or luls her out, apply that as necessary, and if you feel you need a little bit more excitement do whatever makes her excited whether it is earlobe nibbling for massaging her feet.

Basically, just react to her, and have her react to you based on what you know of each other, and you will have a wonderful night.

I miss my Ex, a lot.

Good luck Feral.

Thanks, Wyrmcraft. :)

We're kinky, but we're oddly romantic, too. The rose petals on the bed is probably too cliche for her, but I'm sure I can find a way to add a degree of kinky romance to the night, too.

She may want a drink to help relax her - which I find understandable, provided that it's only a little, not a lot. I myself won't indulge, as I will want to be fully in control, in case she changes her mind, wants to change the pace, or if other factors come into play.

[Feral_Sophisticate]

Here's an update, folks...

It happened. It wasn't specifically planned or anything, but we'd been working up to it over the past two months. It wasn't even a special "date night" (which we'd talked about, but she felt - and I agreed with her - that it might put too much pressure on either or both of us). I picked her up at work, but was indulging her by wearing my doctor's scrubs and lab coat (which are a huge turn on for her). I tied her up and did all the stuff we normally did - which was fantastic, as always. This time, though, she made it clear that not only was she ready, but she wanted to try it.

So we've now satisfied a very large (and fearsome) curiosity of hers, and I've had the "do-over" that I really wanted. She is curious to try and do more, but we'll continue to let the initiative lie with her.

In the meantime, she remains the delightfully and vivacious demisexual she's always been. I am enriched beyond words by having her in my life.

Thanks to everyone who offered their insight and support, both here in this particular thread, and via PMs. I quite needed that.