pennydickless | 09.27.2019 | Reports - Getting Real

Moving on from being a secret sissy.

This sissy still has a long way to go, but s.he wants to thank the Mistresses/Superiors, and The House, for encouraging and supporting h,er in her gradual transformation from being a 100% closet/secret sissy, to putting h.erself out more openly into the world where s.he can explore h.erself. – penny also wants to acknowledge sisters in The House, who are inspirational for the courage they show on their own journey.

Since joining The House in April, penny has made several alterations to life, and engaged in behaviors that s.he probably always wanted to do, but was reticent about. In no particular order: penny now anxiously awaits visit from Aunt Flo and tries to experience all the things a real woman would while on her period – penny induces cramps through (as per instructions), drinking buckets of water, and taking (lots of!) correctol. S.he also of course is now feeling more comfortable with (super-max) tampons, and on the 3rd day of her period, soils her maxi-pad with cherry yogurt (thanks to The House for that suggestion), strawberry jam, molasses, ketchup, and syrup – oh my, what a big mess, but for some reason, it feels wonderful. And although Midol was recommended by the Mistresses/Superiors, this sissy has taken a liking to pamprin – seems to sound a bit more feminine. Thanks so much to The House for introducing penny to Aunt Flo.

Being introduced to Aunt Flo also forced penny to ‘come out’ and buy feminine products – s.he had to share the aisle in the drug store with real Women, who were undoubtedly thinking that penny was a pervert – or perhaps something worse (guilty on both counts). But the comfort penny developed from shopping for feminine menstrual products has now expanded. Recent case in point – this week, this sissy decided to expand female collections and to purchase some shoes. While s.he did not have the courage to go to a shoe/department store to purchase said shoes, s.he did go to one of those ‘alternative’ establishments that sell (all kinds of) interesting fetish wear. Before going to said store, penny had painted her toenails a lovely pink and had fishnet stockings on, which of course s.he had to remove to try on different pairs of shoes – as a result, the lovely Woman who was attending to of course noticed the stockings and painted toenails. Rather than being embarrassed by this, penny was actually turned on (s.he supposes this is another aspect of evolution). Oh, and penny purchased a lovely pair of (red) Mary Janes, as well as some strappy leather sandals, which s.he will wear each day.

This sissy also had an incredible experience having a (almost full Brazilian) waxing this week. S.he made an appointment with a Female attendant at a fairly busy waxing studio – to add to the excitement, penny arrived at her appointment about an hour early – there were about a dozen people (all Women) in the waiting area, at least some of whom were giving strange glances to this sissy, while penny actively (and visibly) engaged in reading the various Women’s magazines in the waiting area. penny of course had kept toenails painted pink for the appointment, and was wearing pink thong panties and pink sports bra. (next time penny will perhaps also insert a plug) S.he of course had to remove this clothing in front of the (young and Beautiful) Female waxer, Who did not appear to be flummoxed – penny can only speculate that s.he was perhaps not the first sissy this Woman had experienced. Although penny is not very hirsute (i.e., no hair on her back), she does (er, did!) have a considerable amount of chest and underarm hair. The chest hair was of course removed (rather painfully of course), and s.he asked the waxer to leave a small strip of hair under her arms (penny realizes that this may not be allowed, and will remove it h.erself if the Mistresses/Superiors require). Although s.he has been adhering to the instructions of The House to keep her nether regions hair-free, there certainly was some stubble on pubic area and some accumulation of hair on sissy hole – the latter was removed (again, rather painfully). However, penny asked the lovely waxer to leave a small triangle on the pubic area, which was accomplished (and it will be exciting to have this grow out a bit). Needless to say, it was impossible for penny not to be aroused during this procedure, but as her sisters and the Mistresses/Superiors are aware, s.he has a micro-penis, and while the waxer did not openly comment on the lack of size (even when penny’s clitty was ‘erect’), penny got the distinct feeling that the waxer was amused – incredibly humiliating (and at the same time exciting). After the procedure was complete and penny left the room, s.he was once again subject to rather curious glances from the Women in the waiting area. The entire experience was wonderfully humiliating for penny.

This sissy hopes to evolve further in ‘coming out’ as a sissy. the next steps for penny will be to shop (in department stores) for both intimate and regular feminine attire, and hopefully get to the stage where she can feel comfortable purchasing makeup, etc.

penny is SO pleased that s.he ‘took the plunge’ and joined the House of Sissify – with the assistance of the Mistresses/Superiors, and of course the support of sisters, s.he looks forward to expanding feminine horizons.


  1. Good for you sweetheart! Those are such exciting experiences! They always make this sissy drip a little bit. The more sissy has tried to do these types of feminine activities in public, the more confident she becomes in her aspirations!!

    Keep it up and, of course, please share everything!!

    Hugs and kisses!!


Something to share sweetie?