I have a client who desperately wants to look like a woman but is terrified of dressing up. On our calls I’ve gotten him to relax enough to try on panties and stockings. He’s not ready for them yet but he dreams of wearing heels one day. Because he is scared of dressing he binges and purges. After we talk he throws out any clothing and toys we played with on the call. This leaves him with the unwanted task of buying these items over and over again. He needs much reassurance that it’s “not wrong” for him to buy panties and the like. Because of his nervousness I’m nicknaming him Nervous Nelly for this story.

NN called me one night shortly after his most recent purge. He wanted to be sissified and fucked. With no panties or dildo I wasn’t sure what to do with him. It was late at night and no stores near him were open. Putting me on hold NN went looking through his house and came back with panties. He always insistes he’s single and lives alone but I suspect he has a girlfriend.

This solved only part of the problem. While NN had his panty fix there was no dildo in sight. Telling me he will “go look in the refrigerator” he put me on hold again. After a few minutes he returned and asked “Will a sausage do Mistress?” I’m not sure I heard him correctly and asked him to repeat himself. He had indeed gotten a sausage.

I started to caution him, encouraging him to look in another room for something better. He was convinced the sausage would fit up his ass. My advice of putting a condom on the meat was ignored. Instead NN tells me he’s going to turn on the tv and look for porn.

While he’s flipping channels he asked me to fuck him with the sausage cock as he called it. What the hell I figure. If the sausage is too big it won’t fit. And if it does, can a piece of meat do much damage? I think about sausages I’ve eaten. Sure they’re dense but they’re not rock hard so hopefully this piece of meat won’t tear his anal cavity.

When I ask if he has lube he tells me he has olive oil. Resisting the urge to laugh I tell him the oil will work. NN starts fucking himself with the sausage cock. He grunts while he inserts it but soon he is moaning.

Meanwhile he’s still flipping channels. He must be sitting close to the television because I can hear a jumble of voices. The voices stop changing and I realize he’s settled on a program. NN is still fucking himself with the sausage. Through his groans I hear a voice from the show. It’s a woman’s voice talking about STDs. Why he wants to watch a show on STDs while fucking himself with a piece of meat is behind me. NN seems happy though so I play along. Then suddenly he started panicking. “It’s falling apart Mistress.” I’m told the sausage had broken in half in his ass. NN is nervous enough playing with his ass and this sent him over the edge. “What do I do? What do I do!”

I remain calm. Using my firmest yet caring tone I order him to slow his breathing. I explain that he needs to either pull the sausage out with his fingers or use his anal cavity to push the pieces out. The STD show is still playing in the background. I caught snippets of words and it seemed the show was a documentary or news program. NN told me he would get the sausage out but had to end the call first. I didn’t argue; he was horribly humiliated.

We’ve talked since and neither the sausage or the tv show has been mentioned. Clearly irony is not dead.

Posted by Vixen in PSO Confessions