Sissy Paula’s First Escort Meet

Sissy Paula’s First Escort Meet

Those of you whom follow My social media platforms (and even read My previous blog post entitled Sissy Misdemeanours) will know that I have a loyal subservient sissy maid named Paula (P for short) whom mainly serviced Me on a domestic basis. After the weight loss targets, hormones implemented, anal training and various events / public occasion “femme” being adopted the next step in the slut training only seemed natural to replace My hard silicone cock in the mouth with a real one.

Along with the fact that placing My sissy on cam and sending “her” out for meets allows additional income sources. So with an online account on Adultwork set up and floods of requests for meets pouring in I set up My sissy P with her first realtime meet with a “client.” Below is P’s account of her encounter which I found most entertaining.


Mistress Tess x


Though Paula has been around the fetish scene for many years, there are many areas where Paula has not ventured before but under the new wonderful journey now under the eye of the beautiful and all powerful Mistress Tess, 2016 opened up new areas for her journey from alpha male to feminised sissy slut.

The latest task took P from his business suit, as Mistress controls P’s bank accounts Mistress is wanting to see new sources of income coming in other than regular office salary. So Mistress demanded Paula earn some money displaying herself in corset on stockings on a popular adult live cam service at the weekend as part of stripping away P’s background. On the first day on cam Paula earned some monies and Mistress was pleased to see them – adding to the “handbag” fund.

But the following day Mistress had arranged for Paula to meet with a one of the callers for a 1 to 1 session! With just an hours notice, Paula had to visit this mans house and make herself available for his use..

At the last moment the man had asked for a particular outfit but Paula did not have that with her, so on arrival Paula dressed in a smart blouse and leatherette miniskirt, under which was a pink satin corset and pink stockings. White heels and small white jewellery finished off her look ideal for a first interview. As soon as the interview started, his hands were immediately over Paula’s breasts and then her stockings and within the first minute were probing inside her pink panties.

Given that Paula had never had any male contact before, it was quite an experience and as he underdressed and sat Paula on the bed, Paula rubbed her hands over his rough hairy muscular body in contrast to his hands exploring the moisturised softened smooth skin Paula now must keep.

At this point Paula suggested changing into something a bit more suitable for the bed and changed out of the blouse and skirt, putting on a tiny, frilly pink babydoll for him to enjoy more.

After standing between Paula’s legs again, Paula kissed his white underpants on the big bulge and slowly pulled them down. Laying on the bed together, Paula placed her red lips over his nipples and make two lovely red lip kisses around them, before using her tongue to have his nipples nice and erect.

As he reached out to play with Paula’s breasts, he loved their new small but obvious forms which are the result of several months of being on hormones, having been eased out of their bra. As he did, Paula eased down and kissed his cock then licked all around his balls and up his shaft to kiss the to of his cock again and loved how his cock was now lovely and erect and twitching with anticipation. Paula helped him along loving the soft groans as he fought not to cum just yet. This was the first time Paula had kissed and sucked a cock so was already into very new territory.

Finally he rolled over and Paula straddled him feeling his cock rubbing hard up against her, feeling his hard cock pressing against Paula’s large glass butt plug Mistress had insisted was in place for the trip – but he loved the sensation and almost cum before rolling Paula off and standing up by the side of the bed, forcing Paula’s legs wide. As he rolled Paula’s pink panties right the way down, he saw Paula’s PA piercing on her sissy slitty glistening away and went into ecstasy with seeing one for the first time..

This helped him to wank himself off fully onto Paula’s crotch soaking her soft things and pink stockings with his cum, before kneeling down and licking them clean. At this point he realised the time had flown as had been having so much fun, leaving him 20 minutes before was due to attend a work meeting, so a quick finish up, shower and change for both of us and Paula then was on her way smiling, tired and very happy.

On reporting later to Mistress on knees, sissy P had to say loudly she was now a proven cocksucker to Mistress and show Mistress the cash taken from the meet to prove attendance, as Mistress controls Paula’s bank account and would know Paula could not have cheated and drawn it out at a cashpoint. The money is being given to charity, but proved the point Paula has to know she is a true cocksucking whore hopelessly devoted to her Mistress.

Sissy Paula xx