Step-Mom Sees you Pegged
5:48 video
You are my step-mom and you are in the process of sissifying me. At this point in the process, you are only locking me up for a week and then jerking me off on Sundays. This month you have been training my ass by sending me to another mistress, named Jodiann. Jodiann pegs me in her office each week, and I haven't been unlocked for my weekly handjobs per her request. The video starts by you explaining that this is Jodiann's last session with me, and she will be pegging me in front of you. You say that Jodiann will use her large, black strapon on me and that it might be difficult. Basically, pretend to talk with Jodiann as she starts her session with me. Jodiann believes that after a month of chastity she will make me cum like a sissy. You reassure me that I'm not ready for that yet, and I will get unlocked after this session and get a handjob, because cumming in my cage means permanent chastity. Once Jodiann starts pegging me, you relax and go on your phone or read, only looking over when I moan or squeal. Halfway through you take off your sandals/flip flops and place them right next to my face as Jodiann continues. Then towards the end of the video you notice my expression and realize I'm about to cum. Jodiann cheers as she pushes my month-long load out of me and you look at it in shock of how much of a sissy I have become. In this video try to be loving but still a little condescending. At the end you can laugh at me and littletalk to me.