Ass Training Fun

Some year ago I was doing a lot of cross-dressing, I had all the gear. I slowly collected everything - buying it all over the internet. I had some lovely dresses, glorious underwear, stockings, wigs, shoes and a big pile of make-up. I was feeling like such a girl and the yearning for cock was getting very strong. I was so hungry for it, wanting to suck a nice big meaty cock, but most of all wanting to fuck one - yeah well up for it. The idea of being shafted by a nice big joyous cock was so strong for me.

With this in mind, I bought a dildo with the intention of training my ass. My thoughts were if I get a real cock in the near future then I just want to be able to handle it without too much trouble. I had done a bit of insertion years before, but it had been a while and consisted mainly of candles, bottles and things. Sometimes very satisfying, but a bit mundane.

Now I set out to get a proper pleasure stick. My mistake was to buy one modelled on a porn-star. Hahaha, it was waaaay too big, it was huge!. It was very lovely though. Big and pink, with a nice head and a lovely pair of balls. No hair, obviously, but the feeling of the material was very sensual. I remember the first time trying to push it in and getting absolutely nowhere. I was slapping so much lubricant on everything that it became hard to keep a grip on the damn thing. I was thinking help - what’s a girl to do?

The real trick is perseverance. I just kept on trying. I also bought an inflatable butt plug. Not too sure if this really helped but it was fun as a practice trainer. I just kept on trying and trying and feeling a bit miserable every time I failed.

So you can imagine my sheer joy when one night the darn thing just ‘popped’ in!. Wow. It was a tad worrying because I felt really stretched. I also got an amazing sexual feeling as the head and ridge passed through my hole. Wow I though as I very gingerly slipped that beauty in. That was my virginity going! Ha so after that I got very expert.