The start of my life as a submissive crossdresser

"First forays into crossdressing and giving handjobs"

I am a bisexual cross-dresser/sissy and have been enjoying my life as such for many years. It all began for me when a friend asked me to look at some of his ‘girlie’ magazines.

We went up to his bedroom and looking through the magazine got Chris really excited and he got his cock out and started to masturbate. I couldn’t take my eyes off his cock and I slowly reached out and touched it and when he removed his hand I curled my fingers around his erect shaft and began to slowly wank him.

I just loved the feel of his cock, and stroking it and wanking him, and as he began to groan I increased my rate and knew he was about to cum. He shot a nice load up into the air, all over his clothes and my hand and arm.

So there we were in his bedroom and I had just made my first cock shoot, and that was how it all started for me. Here we are all these years later and as those years went by I developed my love for being en-femme, for being dominated by men and women and my desires to please.

To continue, it became quite a regular thing for me to go my friend, Chris’, home at the weekend and while Chris would pour through his magazines I would coax him out of his pants, stroke his cock and make him cum.

I really didn’t find the magazines he was looking at all that exciting but I just loved what the girls were wearing – bras, panties, lingerie, stockings and oh… the high heels!

One Saturday afternoon I told Chris that I really liked the girl’s clothes and did he want me to try on some of his sister’s clothes and then it would be like a girl playing with his cock.

Not too much to my surprise he liked this idea and we went into Lyn’s room to see what we could find. We started going through her drawers and cupboards and found some of her underwear. I stripped off and tried to get into one of her bras but it was too small but we had a little more joy with a pair of her panties – they were tight but I could just about get into them. Next, I tried one of her skirts – again, a bit tight and couldn’t fasten it properly but I was so excited I didn’t really care. Chris lost a bit of patience and wanted to go back to the magazine and so we returned to his room and I gave him a long, slow handjob and watched him shoot. At the time, this was just wonderful. I took off Lyn’s panties and skirt but I knew that I wanted to dress again really, really soon.

The next week dragged quite a lot because I really, really wanted to be dressed as a girl while wanking a guy’s cock.

Chris had a new magazine and I got back into Lyn’s panties, a pair of her stockings (nothing to hold them up, which was a problem I hadn’t seen at the time) and another of Lyn’s skirts (still too small to fasten properly). I was so excited I was shaking… it all felt so good; being in Chris’s bedroom, dressed up and stroking his cock.

I was sitting next to Chris and stroking him, working him slowly to shoot and then… his sister, Lyn walked in to find me wearing some of her clothes and playing with her brother’s cock!

If you like the story so far please let me know and if there is interest I will continue my story.

Hugs n kisses,

Sis