(To Clarify as some have asked. Daddy is a She, She is my owner. The 2 of us have adopted the roles of She is the Daddy and I am Her girl. So throughout my posts you may see me refer to Her as She and as Daddy)
While at work I got a phone call that once I got home I was going to be all dolled up for Daddy (Wednesday night).
She had gone out and gotten me a brand new wig (sometimes I put in hair extensions), got me some new breast forms among other things. She also brought back some of my things that I still had in my NYC apartment when she was in NYC last week. Some of those things included my pink sissy dress, so I decided to wear that. I thought the night was going to be just me and her, like it usually is but after I was all ready; makeup, hair, lingerie, high heels, locking wrist cuffs, locking heel cuffs, my collar and locked in my dress I was told that our guest would be here soon.
I was told to pull a chair into the bedroom and put it in the corner and face it towards the bed, then to sit down. I was tied with my hands behind the back of the chair and my feet in high heels bound together and then my legs bound back to the chair. The doorbell rang and out She went to answer the door. I was in the room for about 15-20 minutes by myself.
In She walked with a submissive behind Her on a collar and leash. She strapped on "Pink Princess" about a 5 inch pink dildo into her harness.
All the while just sitting there knowing what She was going to make me do that night my heart was racing. I had a bit of anxiety and lots of nervousness but I didn't want that to show. As I calmed myself down a bit I began to get aroused in my cage. BTW today marks day 48 in chastity.
The submissive was bent over a bench about 10 feet in front me and Daddy asked me how long it's been since She's fucked me. I said, "Over 50 days" Then She began telling the submissive that he better take her cock good otherwise the sissy (me) wasn't going to give him a blow job at the end.
That's when my stomach sank a bit and more nerves crept in. It's been drilled into my head that this day would come and that I HAVE TO DO A GOOD JOB otherwise I don't get to cum on day 66.
Then She stuck her cock into the submissive bound to the bench. She began slow as he doesn't take large cocks and I began to get jealous. Wanting Her to be fucking me. I know that She loves to fuck me and that this was torment. I was rocking a bit in my chair wishing it was me, but with a bigger dick, or Her feeldoe. She then put on a smaller dick that She could fuck him harder with. She would glance at me with these looks oh "don't you wish this was you?"
Smaller dick on, She started to fuck him hard, he was moaning and I was begging silently. About 10 minutes later She stopped walked over to me and untied me. Told me to walk next to the submissive who was on his belling/all 4's on the bench and for me to lay down and put my head between his legs where his cock and balls hung over my face.
Let me tell you, the fear that was in me in that moment. But I was there to impress Daddy. Then She got close and put Her dick in his ass and I was told to suck on his balls while she pounded him in the ass. He was clean shaven so that was nice. I opened up my mouth and sucked on his balls. His cock started to drip cum on my forehead and into my hair and eye. I kind of felt like moaning but I didn't, I stayed to course.
Daddy stopped, backed up and told the submissive to sit up and me get on my knees. She handcuffed his hands behind his back and stood over me from the side and ordered me to start sucking. I could hear Her in the background saying things like, "Is she doing a good job?" Let her know if she needs to change anything" "Teach her, because she has to learn how to suck cock for me" etc. I focused on Her voice and tried to suck his cock the way I suck Daddy's cock regularly.
There I was on my knees, head bobbing up and down and this man's cock. He had a rather big dick, maybe 8 inches and thick. He was already dripping when I put my lips on it. It helped me to keep my eyes closed most of the time. If I started to gag a bit I'd pull my head off of his cock and keep stroking with my hand. I felt like I was doing a good job and every time Daddy asked the submissive if I was doing a good job he would reply with, "Yes, she's a good sissy". But at the same time I wasn't really sure if I was doing a good job. I lost track of time and started to think should he have cum already? I hope Daddy doesn't punish me for doing a bad job.
But then, I hear the submissive saying I'm going to cum and with his cock in the back of my throat he spurts a big load in my mouth. Maybe 2-3 shots and I swallow immediately just as I started to gag a little bit and was getting a bit grossed out at the same time. When I shut my eyes it helps me not be grossed out by the act of what I'm doing. I pulled his cock out of my mouth and kept stroking it as he shot another load onto my face and in my eyes. Only a few drops fell on the bench and Daddy told me to lick it up, so I did.
I was left on my knees and he was escorted out of the bedroom and soon after left.
Daddy came back in the room and didn't say much at first. Maybe 10 minutes later I was on the bathroom floor and She asked me what I thought of him. I said, he seemed nice enough but I don't know what I'm supposed to think about him because I didn't talk with him any.
She replies, "Good, you're going to be seeing more of him". I literally just couldn't say anything, I didn't like the idea of that and still don't. The only aspect of that idea that I enjoy is that I'm doing it for Her. In the next hour or so I began to get a little sad. I had just done something I had never done and it was something very extreme. It's allowing myself to be that vulnerable, that controlled, that owned and it wasn't easy at all for me to do.
After a little while She brought me back to "normal" I guess you could say. One thing most people don't know is that Daddy has what we refer to as a "darkside". Meaning, She knows how to and sometimes will break me. She's done it before and as we went to bed that night I knew I was a little broken. I love parts of Her darkside, as does She. But it's something we are both learning to operate within. Me and Her are great together because our interests are both all over the map and we both push each other. In the midst of pushing each other we find each others boundaries and not all play is cupcakes and candy. Lots of our play is hardcore, envelope pushing that in reality arouses the both of us to extremes.
Day 65, aka May 19th has been labeled "Day of Hell". I already know I'm going to be put through the ringer to earn Day 66, my release date from chastity and no anal. Truth is, I have no idea what She has in store. Truth is I'm scared shitless, truth is I'm aroused by all of that and I know She is as well. Something tells me She's going to break me and make me keep going and push through for Her.
And I will push through for Her.
Here are 4 pics.
1) Me on all fours over Daddy in my new black crotchless panties and in chastity of course.
2) Me dolled up from Wednesday sucking Daddy's cock.
3) Picture of the bows She tied on the back of my dress (Wednesday night)
4) Photo of me right before all the action (Wednesday night)
You can read my Owner's blog at Mistress Tangent
