Cap of the Month - II

Holy God, this was a close one!  There were so many good captions this month!  Ultimately, this girl won my heart.  The forced sissy assignment of an uncaring mistress who is willfully invading my day!  Ugh!  I'd probably cum in my cage!

Great work, T-D Captions!

Re-Blog Wednesday - 11

 

I used to go to lunch with my lady and her co-workers like this.  One time I upped the ante and wore stockings and a garter-belt.  She rubbed my leg and almost ran over the garter snap.  I had to stop her or else the cat would have been out of the bag!

My Life as a Sissy Maid VII

It probably doesn't say anything good about me...

 

but I would love to have a girlfriend treat me this way...

Caption of the Week - VIII

You know, I don't really often consider Gif.'s as CotW, but she's just so earnest while she sucks on that cock.  Holy hell!  I only wish is could match that level of intense cock sucking!

Via :Barbiefication

Retro Caption - 4

Another great old one from Sissy Steffi.  It's a shame that she left the game.  I feel like she had a lot of good work left to do.  Or maybe I'm being melodramatic...

Re-Blog Wednesday - 10

Can't believe it's been 10 weeks already!  In it's honor, time to drop one the sissiest things a person can do!