Before Mistress, there was a girlfriend named "L". She was a natural blonde, 5' 3" (or 160cm) tall with everything else in proportion except for natural DDD (or F) breasts. However it wasn't her breasts that attracted me, she was just so much fun to be around. Perhaps it was my lack of fascination with her breasts that attracted her to me, in any event we hit it off.

She began offering massages as a way to transition from innocent conversation to intimate activities. The massages increasingly focused on my bottom, which I hadn't realized was so sensitive, and my privates. I lay face down, spread eagled to make things easier for her. From my perspective I would enjoy the massage until I got too excited, then I would grab her and it was off to the races. From her perspective, she was teaching me to be passive, to physically open myself to her, to let her do as she wished and to follow her lead. She was also learning the right amount of stimulus to give me, enough that I was interested and compliant, but not so much that I lost control. It was still great fun.

Once she had the massage part down pretty well, she began intercepting me when I tried to grab her. Instead I would find myself still laying on the bed, now face up and receiving a world class blow job. When I had enough of that, I would grab her and it was off to the races.  Eventually she got quite insistent about keeping up the blow jobs, which led to awkward comedies as each of us would try to out maneuver the other.  Eventually I just gave up trying to grab her and let her continue with the blow jobs.  As I eventually was to find out, I never fucked her again!

After I became used to our new form of sex life, one day I found a brand new Nexus dildo on the bed.  L didn't say anything about it, but let me look at it and examine it.  I didn't say anything either, although I wondered what it would feel like. When I was good and excited, she lubed it and slowly worked it into my bottom.  She didn't try to do anything with it, just went about her usual activities.  I was a little more turned on than usual, but nothing out of the ordinary.  On subsequent occasions she started fucking me with it, very slowly and gently.  One day she really worked the dildo and I came like a woman, in a very powerful mind blowing orgasm.  That was it, I was hooked!

L spent quite a lot of time fucking me.  I would lie there naked and passive while she wore her baby doll nightie and bedroom heels and did whatever she wanted with me.  When it came time for her to fuck me, she would get this mesmerized look on her face and bang me for an hour or more.  No, I didn't complain ...  

One day L told me we would be going to a BDSM club, dressed as women. I was so excited that I went out by myself and bought a pair of 5" (or 127mm) stilettos, still my favorite heels to this day. 

So this is the story of  how I became a sissy. When L moved away in 2005, I went looking for a traditional Mistress to replace her.  The latter is the story of how I ended up here.

To be continued.