Pathetic sissy hasn’t actually been inside a woman since 2006. When sissy told a female friend about this a couple of years ago, she responded by “giving” me an inflatable doll as am xmas present. I save “giving” because she decided that she would keep the doll at hers and that I’d only be allowed to use it in front of her.
Our friendship/relationship had already evolved to the stage where I used to do all her cleaning, cook for her when I stayed over, lick her pussy or ass whenever she ordered, and be her toilet when she wanted to pee. I was usually punished if I had an erection while licking her, as she said it was proof that I wasn’t concentrating entirely on her pleasure. She generally used to grant me a brief pathetic spoiled orgasm about once a month.
At the time she gave me the doll, I hadn’t been permitted to cum at all for nearly two months. I had to grovel and beg the doll on my knees if it would allow me to have a charity/pity fuck. I had to describe how pathetic I was and how long it had been since my 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 me to let me fuck it, I was allowed to kiss and fondle it, and eventually permitted to put on a condom and mount the doll.
My sissy fuck was very brief, and having not had any release for so long, it was over very quickly and my tiny feeble sissy cocklette squirted so soon. As you can see, the lady involved was taking pictures as sissy had sex with dolly. Once I’d squirted, she contemptuously remarked that she bet the doll had never felt a thing and had barely noticed my useless cocklette being inside. Then I was made to lick out the condom I used.
This was in 2008. Sissy hasn’t actually had any penetration since then.
Sissy isn’t able to post pics to messages, but profile has link. Thank you, Superior Ones.