For starters, I’ll say that in my mind, the term “sissy” when applied to this caller, really doesn’t fit.  I define the terms this way:

Sissy = Obvious guy in over-the-top, frilly clothing, making no attempts at passing

Feminized = May still obviously be a guy, but the intent is being passable, and becoming as much like a woman as they can

Your mileage may very; those are simply my definitions.  However, since the caller in question uses the term sissy to refer to herself, that is what I’ll use as well.

At any rate, my sissy was going on a business trip, and wanted me to plan some adventures for her.  She and I have a pretty in-depth caller/Mistress relationship, so it was fun to plan her itinerary.

Miss Thing, who we’ll call Sissy X, had never been out in public before.  Also, even though I had sent her scores of you tube makeup guru videos, she was still in need of some hands-on makeup application training.  So I decided that we’d combine a trip to the mall with a trip to MAC.  (For those of you who aren’t following along, I’m speaking of this MAC, not this MAC)

I called ahead, and found out that this particular MAC was one that had private, one-on-one lessons with makeup artists who had been pre-qualified to do them.  The artist would do half of Sissy X’s face, then Sissy X would have to do the other half.   I thought that sounded like a great way to out herself a little, as well as a chance to get some expert application advice.  So she was instructed to call in and book the appointment.

Sissy X is a true slut, I know that the whore in her had visions of twitching her ass down the middle of the mall, in a micro mini, fishnets, and platform shoes.  I dissuaded her from that notion by letting her know that our fantasies don’t always play out in reality, and that a first time outing in a mall setting was probably best suited to something casual that would allow for ease in changing rooms and allow her to blend into her surroundings.  We ended up going with some nicely-cut khaki slacks, a pretty print blouse that buttoned up the front, and heels that did not scream “stripper”.

But before Sissy X got to the mall, she made a scheduled stop to pick up some titties.  I had hoped that she could get some beautiful forms, but the store that I was sending her to had those by custom order only. Since I was feeling impatient, and as this was a rare opportunity for her to get away, we ended up going with bra inserts.  Never one to go small when she can go big, Sissy X ended up getting 42D tits.  She picked up a new wig while she was there also.

So not only did she have a pretty new blouse to go to the mall in, she had new boobies to fill it out.  Her first stop was MAC, and the makeup artist did a phenomenal job.  Sissy sent me pics after, and if I didn’t know it was her, I would have not realized it without really looking hard.  She also got quite the haul, picking up about $500 in product while she was there.

Then it was off to the races at Victoria’s Secret.  It was loud in there, and I had trouble hearing lots of what was said.  But I did have the fun of hearing her tell the sales girl that she was shopping for herself, and asking about what size she needed.

Sissy X had business to attend to, but managed to squeeze in a trip to Fredrick’s of Hollywood to pick up a corset and some assorted other goodies.  I was on the phone with her at the time, and it pleased me that the sales people all seemed to take her in stride.

Her last night on travel, we had a session where I watched her on cam.  She showed me all her pretty things as we talked, and then I let her take her clitty out of it’s chastity cage.  She had not been allowed free play or orgasm for 7 weeks, so I decided it was time to celebrate by letting her release.  And what a release it was!  Sissy X embraces my philosophy that a good girl does not leave a mess, and she eagerly cleaned up every drop.

I let her have freedom to play with it that night, then told her she needed to pack her clit away when she packed her bags for the return trip home.  It was a great adventure, and I’m sure not the last that we’ll have.