Becoming A Sissy Maid (Part 1)

Sammy has always been a submissive sissy slut but she craves more. A message out of the blue one day proves to provide exactly what she needs.

It had all started a long time ago, Sammy had fallen into the sissy black hole years back. Since her teens Sammy always had a strong attraction to men and more particularly a deep love of cock and cum. It was just natural, no real thought went into it Sammy just always knew that she needed to get her regular fix of sweet cum. Not only the taste but that texture and warmth as it dripped down her too.


Although extremely convincing, skinny and small not to mention the addition of a sexy pair of heels, a wig and a nice dress, Sammy was very much real. Unfortunately, most of the people Sammy knew, know her as Sam. Her male mode Sam was becoming much less of who Sammy truly was but she hadn’t really taken the first steps to embrace who she really was in the open. Sure, she’d met up with guys in the past but they always came round her place so had never needed to go outside. 


Sammy had dreams of parading outside in her black fishnet stockings, walking to her car in her red 6 inch high heels with feather around the ankles and that new bright pink micro mini skirt that constantly rises up as she walks, exposing her ass as she takes her time to get into her car. Finally announcing to her neighbours and everyone who she actually was! The insatiable appetite to be able to go out dressed and be used by men grew. The fantasy that surrounded it became far too much for her to mentally take. 


Dressed up, playing with her buttplug, pressing it in and out of her lubed hole Sammy is scouting through her favourite sex meet up site, desperately seeking a dominant male to come round to her place and use her. It’s a late November afternoon, there seems to be hardly anyone online and none of Sammy’s three usual fuck buddies were replying to texts. Getting up to go retrieve something Sammy says to herself “It’s times like these I’m glad I have my nice little dildo collection”. Beep. Sammy turns back alerted by the beep. “1 New Message”.

Curious, Sammy rushes back to her computer and opens the message. 


From: oldergent532


Subject: Hi there


Message: Dear Sammy,


I would like to express how sexy you look in your pictures. I am an older gentleman with an admiration for crossdressers and sissy’s and should you not be put off by my age I have a very interesting proposition for you. 


Look forward to hearing from you 




Slightly confused not knowing what to think Sammy immediately clicks onto oldergent532 aka Geoffs profile, firstly scrolling down to his age “72?!” Shockingly exlaims Sammy. Further scrolling reveals a set of photos showing Geoff, a bald older guy although surprisingly good looking. All of Geoffs photos appeared to be from holidays or from days out which made a refreshing change from been plastered with cock pics and only went on to make Geoffs proposition more interesting at least. 

“Should I message back?” Sammy asks herself. Further investigating of Geoffs profile Sammy begins to read a feedback section from other users that had encounters with Geoff in the past:


“Lovely guy knows how to treat a girl with respect”


“Had a hot time with oldergent532 great as always”


“Genuine and kind look forward to next time”


Were just a few of the feedback Geoff had received out of a list of about 10-15. This only added to the intrigue but Sammy couldn’t help but think Geoff was almost double her age. At 37 Sammy had never been with any older men and to be quite honest was slightly intimidated albeit excited by the thought of meeting and been used by an older man. The question still remained though what was this proposition? Dying to know what the proposition was Sammy promptly responded to Geoffs message.


From: sissysammy


Subject: Hi


Message:  Hi Geoff,


I must admit I was surprised by your message but flattered that you like my pictures :) No I’m not put off by your age would love to hear your proposition ;)


Sammy X


Message sent. What could he want? She knows he’s seen her dirty pics. He seems like such a respectful and genuine man. Her mind begins to race. Making her hornier at the thought of pleasing and getting fucked by an older guy, much older than she’d ever let fuck her before and continues to play with her buttplug whilst eagerly awaiting the reply.


“1 New Message”


From: oldergent532


Subject: Hi there 


Dear Sammy,


That’s great to hear. Sammy I would like you to come to my address dressed in slutty maid attire, the sluttier the better and allow me to watch you carry out some light chores dusting, hoovering etc. I will pay you for carrying out these services.  


Kind regards 




Even more intrigued by this proposition Sammy began to think about what Geoff had just asked. He wanted her to go already dressed. Maybe this could be her chance to openly go out dressed in public and be seen. The thought of going to his house dressed up like a slut and been watched whilst she carries out these duties somehow appealed to her appetite to further become a submissive sissy slut. What would happen afterwards? Getting paid by old men? Would he fuck her? Could she suck his cock? Who knew but Sammy certainly couldn’t forget the idea responding immediately to Geoff, expressing her interest and requesting more information that would lead her on this new path of becoming a sissy maid.


Click here to read Part 2 of Becoming A Sissy Maid.



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