My friend has had partners before, but she’s still virgin and wants to lose it with me

Tl;dr at the bottom

I (27MTF) met this girl, (F27), through an LGBTQ group a few months ago and we quickly became close friends.

Although I’m attracted to her, I never said anything nor made a move as figured I wasn’t her type (she was quite flirtatious with the other girls, not with me). As our friendship deepened we bonded a lot with how we like to show affection for one another, we’d cuddle all the time, talk about anything, share secrets and fears, she became an integral part of my life and she makes sure to let me know I’m part of hers. Not with what she *says,* but through things she *does.* I’m special and I know it. Yet, sex and intimacy was one thing I never even considered happening, as through everything she said, it was clear we were complete opposites in that regard. My other friends would often tell me that this was going somewhere, but I always assured them she’d never want anything with me and repeated to them as much as to myself: *I can’t provide what she’s looking for and she doesn’t want what I have to offer*

Boy, was I wrong

During one of our phonecalls she were telling about a medic appointment where the doc told her she’d “be able to have sex with her boyfriend soon” and she laughed at the thought of a boyfriend. Then, in one of our moments of silence she quietly sang that *”(I) would have sex with (her)”.* Thinking it was just her being playful, I told her “don’t joke around like that because I tend to believe it”, to which she said “but seriously, I was thinking about it and I think I could do it with you, if you wanted to”

Seems quite normal, until you learn just a few things:

– She’s terrified not only by men, but penises as well. She once said she could see herself with a transwoman, but it would take her a while before she could muster the courage to touch “it”.

– She has **severe** body image issues to the point of dreading medical appointments where she might have to take her clothes off (I literally begged her not to ditch that last one)

– She had quite a lot of sexual partners already, mostly cis women, which she is not ashamed of talking about, but *none* were allowed to even touch her there, it was always her doing the busy work. As she sees it, she’s a virgin.

And she’s seriously considering *me.* It’s almost unbelievable. I feel like the most special, most important girl in the whole world. I’ve seen her on the verge of tears when talking about her frustration with her inability to have sex, and now here I am.

I accept it, I **WANT** it, no questions there.

She’s been slowly talking more about it when we see each other, setting her boundaries and expectations. She’s also being more flirty and playful to get herself used to the idea, often joking and exaggerating my size (she’s never seen it, but I mentioned it once, way before any of this), it came to a point where I offered to show her a pic on my phone to show her it’s no big deal, but she refused, a bit scared. I can see she’s still struggling with it, but that it’s a fear she wants to fight and overcome, so she can call it off anytime and I won’t blame her, but I won’t back down on my own. (She even warned me already to not be too gentle and only stop if she specifically tells me to)

“Where’s the problem” you might ask?

**THIS IS PUTTING A FUCK TON OF PRESSURE IN ME AS WELL**

Yeah, I’m happy, I have the opportunity to share possibly the most special moment of my most special friend’s life… and it’s also in my power to ruin it or make it mediocre.

Not only am I transitioning, which has lowered my testosterone to a quarter of my former levels so far (and decreasing), but I also asked my psychiatrist to switch me back to meds that would kill my libido, and they’re mostly working (that was before she proposed that)

And if all that wasn’t enough, we are opposites in bed: she likes it rough and I lean into romance. It’s a territory I have next to no experience on, although I’ve been doing some research.

I wanna be there for her, for me as well, but I’m terrified that I just won’t know how to please her and that I’ll let her down. Or that I won’t get hard at all. She’s putting so much trust in me, what happens if I fail to deliver? I know she hasn’t said it in these words, but I feel she’s putting her hopes on me and although I’ll do my best, I don’t think it’ll be nearly enough what she deserves.

I guess what I want to know is how I can forget this pressure and just think about it as sex

Tl;dr:
Friend with body image issues who never trusted any of her former partners to even touch her privately has talked about and planning to lose her virginity with me: a very close and trusted friend, but nothing more yet.
I am flattered and empowered, but cracking under the pressure of knowing that it’s all in my hands whether she’ll relieve her frustratrion or become more hopeless about it