Earlier in the evening Mistress informed me that we would be having a play-date with another sissy. I was initially surprised and a little nervous but as it got closer to leaving to go to the dungeon, I got more and more excited. I was so excited that I actually got dressed in my full sissy wear before leaving, forgetting that for the first couple of hours of the night I was a demo bottom at a cbt station, and my Josy persona was going to have to wait. I literally had to change in the car back to my boy clothes while she drove to the event. With Movember behind us I realized, it had a been a while since I had dressed up and I was excited to be my Josy self again.
After two hours of kicking, kneeing, crushing, caning and for the first time ever, the excruciating feeling of BenGay, my sissy balls were aching and I was happy have them once again protected by my chastity cage, where I know my sissy clit belongs. The other sissy that Mistress had organised our play date with had been popping by to talk/flirt with us all night. Mistress had locked her up for the evening just for fun and I had to admit, despite not often finding other sissies hugely attractive, I really did think Chelsea was cute, and looked wonderful. Was I crushing? Definitely and was excited for whatever Mistress had planned.
I was told to change into my maids uniform and as always I felt so very pretty in my petticoat, pink panties, and pristine white lacy gloves. I got such wonderful and positive feedback as Mistress paraded me around on her collar and leash. The other sissy found us and Miss ordered Chelsea to change into her maid uniform and she came back looking very slutty. My maid’s uniform is prim and proper. If it wasn’t I’d be too distracting when Mistress is trying to work while I’m cleaning.
We both sat at her feet and Mistress knew we would do anything she wanted or needed. One thing I definitely liked was that like me, Chelsea didn’t seem to be doing this for humiliation purposes, but purely because it was fun, and incredibly hot.
We were ordered to head over to a spanking bench and link hands facing each other. We looked each other in the eyes and Mistress spanked us, with our skirts pulled up. Mistress told us we were sisters. Yay! Finally a sissy sister to share the spankings with! We took our spankings before Mistress had us practice some submissive positions. This is always about power, control, and obedience for Mistress so I know she enjoyed having two sissy girls kneeling at her, literally worshipping the ground she walked on.
“Josy, you have one chance to ask Chelsea the question I know you want to ask and if you ask the wrong one, you will get 100 spankings right here!”
I’m never one to turn down spankings but I thought about my two hour tear inducing spanking less than 24 hours previously. Mistress and Marissa had bruised my ass, I wasn’t sure I should be cheeky and get it wrong.
I timidly looked the taller, more curvaceous sissy in eyes again and asked…
“Chelsea, may I please suck your cock?”
I hoped she would say yes and moments later my wish was granted! I was on my knees as I begged Chelsea and Mistress for cock. It didn’t take long before she was hard and ready. I slid the condom down her cock (always safety first) and began sucking. Her cock was a nice size, and I was able to take it all in my wet mouth. Mistress says practice makes perfect and I was enjoy practicing deepthroating for her pleasure.
My head was held in place but there was little gagging. I made sure to suck cock just like Mistress had taught me, and I hoped I could make her cum. Unfortuantely Mistress likes to tease me and keep me wanting so only allowed 5 minutes of sucking. I knew these minutes would go toward my 169 minutes of sissy cock sucking training (69 minutes left!) I thanked Chelsea before kissing her shoes as Mistress ordered and looked on proudly.
We cleaned up, I got changed and headed back out into the real world. I thought that 4 am was bedtime after such an eventful weekend but Mistress was obviously still feeling excited as she allowed me to worship her pussy before using the dildo to give her two powerful orgasms. I feel asleep next to her, feeling like a well used slut.
She mentioned something about having an 11 inch cock give me a facial later tonight as she drifted off to sleep…
What have I gotten my little sissy self into?!