Hiya. I have lurked on the forum as a guest for a time, but really need advice from anyone who has been in a similar situation, or any sensible suggestions if not.
I'm Amber, 22 year old TV. I've dressed from as far back as I can remember, and since moving to London 2 years ago I'm Amber from the minute I get home from work, to the next morning. I have zero interest in transitioning, I'm a guy with a strong feminine side.
I had always assumed I was pretty passable, although at 5 ft 10, I'm tall. No one had seen this side of my persona.
In June, my closest male friend, Robert, phoned to ask if he could stay a few months while he did some studying in London. We went to school from the age of 5, and although I left Manchester, we've stayed in touch, and see each other when in respective cities.
This presented a problem.
My flat is fairly small.....he'd have to sleep on the couch in the front room. No problem there. But Amber's closet and things are not the easiest to hide to someone staying over for that length of time.
The way I saw it, I could refuse to let him stay......put Amber into storage for a few months......or tell him.
I decided to let him know. If I couldn't trust my best friend, who CAN I trust in the world. I think also, I've been so closeted for so long, a part of me WANTED to share.
So, I picked him up from Euston, took him for a coffee, and basically told him. His face was a picture, and I said if it was a problem I understood if he wanted to look for other digs.
Fortunately, once it had sunk in and the jokes were over, and he'd promised on pain of death not to share - HIS concern was more for me. ie would I stay in my room when dressed...did I want him out when I did etc.
I told him I was cool, as long as he was. Long story short, and the hardest part, was dressing for the first time and letting him see me, which occurred about a week after he moved in. I'm fairly conservative in my dress sense, and stuck to skinny jeans, heels, top, makeup etc. He admitted he had been expecting a Lily Savage style appearance...common misconception......and was pleasantly surprised.
Anyway...... since then I've dressed pretty regularly at home, not as frequently as I usually do, but 3 or 4 nights a week. On those nights I'd usually cook supper, and we'd watch movies and chat etc.
I relaxed into my full wardrobe......skirts, dresses etc.
He has finished his studies.....and goes back to Manchester on Monday.
Yesterday, he went off to see friends in Bristol...and is back on Sunday.
He suggested we had a farewell supper on Sunday night...and asked if Amber would do the cooking.
When I got in from work.....I found he'd left a present for letting him stay.
Lingerie. A lace bra, panties, suspender belt and stockings. His note said he'd checked sizes in the draw, and hoped I liked them.
They are beautiful....very subtle.
And here's my dilemma.
Although I identify as hetrosexual, and have to this date never been with anyone who isn't female. I HAVE fantasised about being made love to by a man.
I had expected a gift to be a book...or DVD etc. Lingerie makes me wonder if he has ulterior motives. I think it's the belt and stockings that make is seem somehow...more. As soon as I think he MIGHT, I find myself excited and dry mouthed.
He's back on Sunday, he's asked me to make supper as Amber, and I find myself thinking "I'll wear the lingerie and a nice dress".
I'm terrified that he might want to make a pass at me.....I'm equally scared he may not. I don't know if he has ever been with a "man".
On TOP of that...I don't know what to do if he DID.
Would it damage the friendship? And if he did, and I went along with it......I've never taken the female role in bed. I'm scared of not being able to satisfy. I know the moves...lol....but would I be able to please?
I suppose the advice I'm looking for, is ...am I reading too much into what could simply be a gift? Will I make a fool of myself if I basically flirt like an idiot?
I'll shut up now.....but would appreciate advice...particularly from any girl who has faced a similar problem.
Thanks
Amber.

Sunday came and went, and all resolved! x

And the resolution was what?

Not fair to get us involved in your story without giving (discreetly) the final chapter. 

Smiles. Sorry - didn't think!
In short, and discretely..... we demolished a bottle of wine. Strange vibe all night. Around midnight, he asked if he could *see* his present. I stripped to show him, and we kissed. Ended up in my bedroom. A lot of fumbling. A lot of uncertainty. Mainly on his part. It didn't take long before he was satisfied in the simplest way. We fell asleep. He woke and went back to the couch in the sitting room. I lay awake for a long time. We had a stilted conversation over breakfast. He left.
We've spoken on the phone since, and two things are very clear.
One - NOT the best idea to sleep with your best friend. Two - despite it being an unsatisfactory, completely unromantic experience, I DO intend to explore that side of my sexuality again.

I'm sorry your experience did not go as you wished it would but I wouldn't give up so fast.  It probably was a bad idea to experiment with your best friend and someone you have known for a long time in another way.  Sounds to me this may have been his first experience too.  I can't believe it would be anything but awkward. 
From reading reading your initial post I think this is something you have fantasized about and you would like to experience a romantic evening and love making from the female perspective.  You picked the wrong guy this time but it doesn't mean it won't be better next time.  Learn from the mistakes you made and move on.  I've been with guys that made me feel like a guy in a dress and guys that made me feel like a woman.  It's really great when you find a guy that gets it and gives you a moment of sanity...where things are how they are supposed to be.

Hi Julie...absolutely. I think it was circumstance and opportunity that presented itself, and I thought I had *one chance*, and it had to be taken! On the flip side, I was able to spend time prior to that as Amber, in a way I had never been able to with anyone, and to be accepted and understood was a huge thing for me.
In any case, we are back on an even keel in terms of talking - and yes, it was a fresh experience for him to, and in his words *tried it - won't be going there again!*. LOL.
I'm just pleased I can smile about it!
Thanks for the kind words.