And I thought I left it late. Your story sounds very familiar Mr Ardiles. I was just turning 28, never had a gf long enough to get to sexy times and realised I really needed to get started, never exactly a pussy magnet myself a WG was the easiest option.
I don't want to give you the jitters but it almost certainly won't go well, but you should do it and resolve to go again quite soon after.
Here's my "awkward popping cheery with escort at ripe old age" story, probably like many others on here but fuck it... one more to the pile.
I had texted earlier in the day to arrange, the AW profile said not to text but I was too nervous to call so gave it a punt. She replied and all was sorted for a 10pm booking. The maid opened the door, she was young and cute and giggling, she led me to the bedroom. The WG was nice, Polish, older than her pictures suggested on AW which was a little bit of a turn off but by no means ugly or fat. She was professional and put some effort into it, she had just had a shower before I got there, her hair was still wet, I think she expected me to be late. I simply stated it was my first time but left the impression it was my first time with an escort. She took the lead. All was going well until the rubber went on. I'm not massive but it felt tight and I lost all sensation. Started in missionary - I could barely feel a thing, I had to look down to check I was inside her!
I've since concluded that she might have been a bit loose, but also years of wanking I had conditioned Mr Wiggly for more tactile stimulation than what I was getting here. I was going a bit soft so she whipped off the condom and started sucking away. She then commanded me "now you cum in my mouth" - my nerves kicked in and before you know I was soft as could be and numb in every respect. My mind was reeling, I was panicking - turns out I'm not a stud as all the porns suggested I should be.
Here's the bit that I've since realised this girl was perhaps unusually sympathetic. She tugged away at my now very maliable wormy thing for a while, she even commanded me to have a tug myself but my nerves were in charge now. She got up and said I needed to see a doctor. Can't honestly remember what I said to that, she asked in broken English if I liked the maid? Slightly stunned I said "yes".
She walks out and in comes the maid, now very much not giggly, slightly put-out but proceeds to undress, (she had amazing boobs but not great in the face department, but cute still). No English what so ever but somehow I'm on my back and she's sucking away. I still couldn't "cum in mouth now!" but did manage to tug off a facial while standing over her - which she really didn't want by the look on her face just before, but perversely that actually helped me I think.
As I was leaving I gave her another 20, but the whole thing was kind of a blur, I don't remember leaving the place or getting into my car.
I laugh and cringe at the whole thing as I'm sure most do but I don't think I'll ever forget it.
The main thing I took from it is that it is by no means as amazing or life changing an experience as you think it should be. Days later I was dealing with women easier thinking - it's no big deal, "you have no mysteries of power over me", even though the experience was very awkward.
The only thing I wish I had done was to go again somewhere else very soon after (too embarrassed to show up there again!). I left it another year before going to an escort again and to some extent the whole thing played out the same - just without the cute maid ending.
The only time I've felt comfortable enough to cum was when I went twice in a week (two different girls), the first visit, didn't lose wood but just couldn't cum. The second time I was in a "fuck it who cares" mood and it worked. I wish I had kept that up as I've since had the same trouble and it puts me off for months and sometimes years between visits.
This is still an issue and very much why I'm on this forum as I need to get back on the horse and get my head straight and confidence in the this department up.