Patheticsissy hasn’t actually been inside a real woman since 2006. When sissy told a female friend about this a couple of years ago, she responded by ”giving” sissy an inflatable doll as an xmas present. Sissy says ”giving” because she decided that she would keep the doll at hers and that sissy would only be allowed to use it in front of her.
Sissy’s friendship/relationship with her had already evolved to the stage where sissy used to do all her cleaning, cook for her when sissy stayed over, lick her pussy or ass whenever she ordered, and be her toilet whenever she wanted to pee. Patheticsissy was usually punished if sissy had an erection while licking her, as she said it was proof that sissy wasn’t concentrating entirely on her pleasure. She generally used to grant sissy a brief and pathetic – and usually spoiled orgasm – about once a month.
At the time she gave patheticsissy the doll, sissy hadn’t been permitted to cum at all for nearly two months. Sissy had to grovel and beg the doll on his knees if it would allow sissy to have a charity/pity fuck. Sissy had to describe how pathetic sissy really was and how long it had been since sissy’s last fuck, and plead to be allowed into the doll, all while being watched. When she decided the doll was convinced and was feeling sorry enough for sissy to let patheticsissy fuck it, sissy was allowed to kiss and fondle it, and eventually permitted to put on a condom and mount the doll.
Patheticsissy’s fuck was very brief, and having not had any release for so long, it was over very quickly and his tiny feeble sissy cocklette squirted so soon. As you can see, the lady involved was taking pictures as sissy had sex with dolly. Once sissy had squirted, she contemptuously remarked that she bet the doll had never felt a thing and had barely noticed sissy’s useless cocklette being inside. Then sissy was made to lick out the condom sissy had used.
This was in January 2009. Sissy hasn’t actually had any penetration since then. This is sissy’s only fuck in the whole of the past six years. It’s doubtful that sissy will ever be inside a real woman again as sissy has become even more submissive and pathetic. In fact, sissy probably couldn’t even fuck a plastic doll now as sissy’s cock is now only about two inches soft ans three inches hard. And most often too soft to use.
Submitted by patheticsissy