I shop. Therefore I am.

Shopping for a Sissy

jillie | 06.08.2017 | Reports - Womens Studies

To the Honor and Benevolence of her Mistress:

jillie is very new at coming to terms with her long-hidden feminine feelings. She is trying to focus her wandering attention on all the wonderful material and lesson plans that Mistress and her Staff have placed on this important, yet very intimate, Site. Shopping is turning out to be a real problem for her. So far, she has ordered every piece of girlish clothing she has from online shops. She really does not know if she has the innate courage to going shopping for lingerie as a male. She blushes very easy and her face turns very red when she is embarrassed. She is sure she would mumble some words to the clerk and quickly exit the store. But, jillie loves being around women and now that she is wearing panties and stockings, so far, she is becoming addicted to the gentle and sexy tactile sensations that her legs and crotch experience. She will continue to order from online shops and she has signed up for lingerie catalogues. jillie wants to wear lipstick and take a beautiful, scented bath but jillie cannot bring herself to buy these articles in person. There is no doubt that she has an intense wish for a girlfriend to go shopping with her so that she can fulfill these erotic feelings and titillation. Alas, this is not the case at present, and jillie is forced to move ahead on her journey by herself. She hopes that her Mistress understands the situation she is in. jillie is very excited about the new articles of clothing that arrive in the mail and she absolutely loved the tactile sensation of putting on her first pair of shear stockings. She often feels very dumb regarding women’s clothing. However, she pays much more attention to women when she is out in public. She wants to be closer to them as they shop and she can see now the pleasure they obtain from shopping. jillie recalls sitting in the women’s section of Macys and waiting as her ex-wife shopped. It turns out that jillie seems to have good taste in women’s clothing and always picked the right blouse or outfit for her ex-wife. She does admit to purposely avoiding the lingerie and makeup counters due to her embarrassment but she did like walking past the pretty salesgirls and salesladies. Please consider this the first of most likely many chapters of jillies report on Shopping. She will submit a report at every step she takes in this delightful journey. She, again, begs her Mistress to have firm patience with her. If jillie had a Superior, she would demand a spanking for her timidity.

Please accept this first of many updates with the sincere subjugation and humilitation of one her Mistress’s lowliest wenches-jillie



Something to share sweetie?