My first time
I suppose the best place to start is the beginning. I'm not shy and have always been happy to take the initiative and its always been that way , apart from my very first experience. I started wearing female clothes when I was 16 and have worn female underware all the time since I was 17.From that age I have always been fully shaved. I have never had any interest in females and even as a very young man my thoughts and fantasies revolved around cds and cute guys.
My first experience of any note was when I had just started work, I was under 20 and was working in an office.We had lots of visitors such as factory staff, visiting tradesmen, drivers etc who were connected with the company and my experienced incvlved one of these. I must have been giving out the 'right signals' as they say as a man who was older than me , probably 35 or so 'came on' to me . Without being explicit or even mentioning sex we had a couple of quite intimate conversations and he asked if could visit me in my one bed flat.The only thing he did say as to suggest directly some sexual activity was to assure me of his discretion, and the discretion he expected too. A time was agreed and I had a couple of days to prepare myself.
I gave it some thought and wasnt to sure how to 'dress'..if at all......in the end I decided on just a black bra and panties.When he arrived at the expected time I was wearing a dressing gown over my underware as I answered my door.
After a 'hello' he took the iniative and kissed me, it felt so right and even though I could have let myself go there and then I ushered him into my bedroom, it seems so strange now but I said words to the effect of 'you can get ready in here'....and I left him to get ready...thinking to myself 'am I sure I want to do this '....the first and only time I ever questioned myself.
After about 3 or 4 minutes , I asked if he was ready and he relied yes, as I entered the bedroom he was there laid on my bed, naked , rubbered and was putting some lube on his excited manhood.
I was still in my dressing gown and I sat on the bed with my back to him as I disrobed....I remember thinking....'he can see my bra straps'....it semed a big deal that another man was seeing me in my bra.
I unfastened my bra and took it off, then stood up and my dressing gown fell to the floor, as I stood up with my back still to my 'date' I bent over slightly and removed my panties..at the same time thinking 'he can see my bare bottom !!'.....he then made his move and pulled me towards him, I was totally naked as was he and it felt so right ...he asked if it was my first time and I said 'No'...which was'nt true
After some brief but very pleasant kissing he turned me on my tummy and entered me ....I was being taken by another man and it was the greatest feeling I could have , I found my body rythms matching his and it was'nt very long before I heard him groan and cease thrusting as he creamed.
Turning me over and embracing me, he took a hold of my manhood and gave me a happy ending.........I think I expected more , like him telling me how much it meant to him...but he didnt though he politely thanked me and suggested we must do the same again...though we never did ...and within a short time he was dressed and gone ..............I only saw him twice and very briefly aftr that , he just have me a wink on both occasions.If I ever have a rendezvous and I know or suspect its their first time , I always try and make them feel a bit special.......though even looking back, even now, I remember feeling good that another man wanted to take me ....
Now , many years later , if I happen to be sat on my bed in my dressing gown ...and I take my bra off before bedime .....I do occasionally remember that time .