I absolutely adore My femme callers! Now, I make the distinction between someone who is a crossdresser, a sissy and someone who is a T girl or transgendered ( real girl but with some so called male parts). I know that not all panties are the same!
That said, I was looking at some of our sister oriented sites and realized that THIS sissy training is My last post on sissyville! OH NO! I need to do more assignments there. For that, I want your help! What kinds of assignments do you want to see from Ms Olivia? Post your comments here or send Me an email.
I got to thinking about this because of naughty sissy dressup play! I love to give crossdressers and sissies a makeover! In fact, that is part of the sissy school training program.
I recently laughed when I got a blog comment about one callers fetish! And, that inspired this blog post about the importance of pretty hands on a sissy! I’ll admit, when a sissy has lovely long glossy nails those hands are in perfect shape to stroke and hold a cock in the most feminine way! Being feminine while still being naughty is important!
When I dress a sissy
When I give a sissy a makeover I pay attention to everything. In this case, sissy is wearing a fantasy wig because I felt like French renaissance elegance (and debauchery). ~grinz~ You just wait to see what trouble this pretty sissy gets into with her new friend!
One callers sissy fantasy with elegant sissy nails
hi Mistress Olivia. i admit that i have something of a smoking fetish. not the healthiest habit i know, but i smoke only occasionally and then only when dressed. there’s something that turns me on about lipstick, fingernail polish, several rings on my fingers, and a nice, long, girly virginia slims 120. i only smoke 120′s of course, and it’s so sissyish also to have a cigarette which when unlit is longer than my sissyclitty (giggles). it’s a simple thing also, but i also luv being addressed as sissy or pansy, sort of like being conditioned and trained to regard the terms as natural and completely fitting for me. thanks
To the caller who inspired this blog post, I want you to imagine that the lip gloss wand that lovely girl is wearing is your favorite girly Virginia Slims 120. Now, what will sissy do next? Hmmmmmmmm?
For other sissies, give Me some of your favorite assignment ideas and you’ll find them on sissyville in the …. ahem … cumming months!
If you need help finding the perfect Mistress for you, just ask the lovely Ladies on the Live Help Desk.
that is so me in picture of you doing that to me. I’d love for you to do that. How can I say no? I can’t. I’d love to have you on phone to give me assignments. To go to Victoria’s secret with you on phone taking to salesgirl putting lipstick on me spraying me in perfume/lotions having me get fitted for bras. What are we waiting for. I have credit card in place where I can call weekly. We can do call at Victoria’s then later at home you can get me off in hot fantasy when you did dress me as girl.
I would love to talk with you again peter and turn you into My lipstick lesbian ~smiles~
That would be awesome. Days are so tough. Sunday’s can work. Nights work better but I know you work in day time. We should be able to figure something out. This post as well as picture got me wet hard and off. It totally reminds me I’m your sissy girl who has no say in matter with you dressing me. I just have to find day/time to call. Also would love to do mistress calls with you Ms Violet as well with other mistresses.
YAY! I’m so glad you liked the post and the photo! ~grins~ I do know what to do with you….don’t I you lovely lesbian sissy?
Oh yes I’m puddy in your hands. The wig is hot. I’m sure you would have that on me with no way of taking it off along with makeup bra lipstick dressed perfume lotions. It’s only fantasy but I really want that to happen for real. Sadly it won’t. But I have dresses as well as every thing else at home. I want to do 2 mistress calls with you and other mistresses Turning/dressing me as well as getting me of and staying that way.
One thing that I do in the phone fantasy is to super glue that wig on you! ~grinz~ There will be NO WAY you can take it off peter! You’ll be our lipstick lesbian forever!
I’m not sure if this really counts as an assignment, but I have a half-formed fantasy roleplay scenario that I’ve been thinking about lately…
Two of me early cross-dressing inspirations were from school. This was in the 80s, in Britain, where school uniform was (still is) the norm. I was so envious of the girls in my year with their neat, fitted pencil skirts and always wanted to spend a day dressed as one of them to know what it felt like.
I also had a math teacher whose fashion sense and sheer femininity I was in awe of. She wore the highest heels with beautiful tailored skirts. I was slightly scared of her, but in a way that I found slightly exciting…
in my fantasy scenario I am the new ‘girl’ (18 of course), dressed in pencil skirt and stockings (yes, the girls did wear stockings… I know that because they liked to tease the boys about it) and pretty kitten heels. My teacher, dressed to the nines as usual, keeps me behind after class because something doesn’t seem quite right to her. She questions me and figures out who I REALLY am… and threatens to reveal my secret to the school… unless… I do EXACTLY as she says.
I am very scared but unbelievably excited and turned on and promise to do whatever she wants me to do, so long as I can continue to be a girl and enjoy the feeling of my skirt, stockings and heels.
Hmmm. What, I wonder, would my teacher have me do? 😉
Ummmmmmmm, that is a wonderful roleplay idea sara! While I don’t think I could pull off being a math teacher (grinz) I know lots of things a teacher can do to make sure that students …. ahem …. do ALL of their assignments! ~smiles~ THANK YOU for your comment!
what site did you get wig/corset from? That’s hot. It would look good on me.
peter, just take a look at all the options when you google wigs or corsets….there are SO MANY options in terms of price, style, etc. You can find exactly what you want and the thing that is perfect for you!
as hot and sexy as you are why would any sissy say no to you.