I gat a text from Mistress..” Meet me at the hotel room 224 at 6 be clean and ready to play”. Awesome I thought it had been a while since we had a good play session and especially at the hotel we frequently play at when the house is not completely empty.
I showered did a touch up shave as best I could considering I’m currently locked in our 6000s and headed downtown. As I went to knock on the door I noticed it was slightly ajar so I slowly opened the door and saw Mistress sitting in a chair in the far corner of the room. She told me to come in and fix her drink and pour myself some Bourbon. As I handed her drink to her she simply said, “Show me”. I replied “Yes Mistress” and undid my pants and let them fall to the floor standing in front of my lovely Mistress in panties covering my chastity. No matter how many times I do this it sends a bolt of humiliation right through me but makes my cock strain against its confines every time. A lovely smile came across her face as she reached out with both hands and puled my panties down to mid thigh and then held my locked cock in one hand then leaned forward and kissed the end of my locked cock.
“Pull those up and sit with me” she said. We talk for a while over our drinks and she told me that we had been slacking on my training and the goals she has for our relationship. She talk about the “events” she plans to host- but we’ll save that for another post. She said that in addition to continuing my training to suck cock she really wants to watch me take a real cock in the ass for her. She went on to say she thinks I might be a little out of practice. Although I do wear a plug extensively I have not had her strap on in some time. But that is going to change tonight she informed me.
She told me it was time to get into the right mind set, she has been increasing the degree of cross dressing lately. She told me in the dressing area is a bag and instructed me to put everything on including the restraints but don’t lock them. When I finish bring the gag, blindfold and locks and kneel if front of her. I began to get dressed first new matching panties garter and stockings. A short skirt and tight sweater along with four inch heels. I still have trouble walking in them but I do ok for short distances. As I got the leather cuffs out I noticed on the counter in the bathroom a wig and knew exactly what it was for. I put the wrist and ankle cuffs on and then placed the wig on my head and adjusted it as best I could. I caught a glimpse of myself in the mirror, didn’t look great but at the same time didn’t look bad. I looked in the bag but could not find my collar, which I thought, was strange. I grabbed the ball gag, blindfold and locks took a deep breath and headed out to Mistress.
“Don’t you just look adorable” she said sending embarrassment and humiliation cursing through my body. She motioned to turn around and kneel. I sunk to my knees with my back to her. Without a word she placed my collar around my neck and locked it on with a small padlock. She locked the cuffs and told me to stand and go over to the desk. The desk was really just a narrow high table jutting out from the wall standard hotel type furnishings. Standing in front of the desk she came up behind me and pushed me forward forcing me to bend over the desk. She secured my ankles to the lower legs of the table and then put thick leather thigh cuffs on me and secured them to the upper table legs. She the secured my wrists to the other end stretching me bent over on the table. Next was the ball gag also locked with a small lock.
Standing behind me caressing my pantie covered ass she said that we were going to do more than just work on getting me ready to take a cock. Panic gripped me and I must have struggled a little because she promptly smacked my as told me to be good and “take it like a big girl” followed be her rather evil giggle. She then pulled my panties down and lubed up my ass and placed a good size butt plug in me. Pulled my panties up and gave me a smack on the ass. She proceeded to show me a note she had written that said “You can have her ass – mouth and locked up clitty are off limits. She is to remain tied as you found her. NO EXEPTIONS” I tried to plead with her desperately but the gag prevented anything from making sense. She tucked the note in partially in my panties and set a few condoms and a bottle of lube next to me and then put the blindfold on said she was going down stairs to the bar to find a cock for me. The door closed and I was left in silence.
After a few minutes desperate panic set in and I struggled but there was no way I was going to get out of these bonds. I franticly mulled over possible scenarios over and over in my head with intermittent struggling. The scenario’s ranged from she is just fucking with me to I’m really going to take a cock in my ass and everything in between. I am not sure how long I physically and mentally struggled but it all came to a screeching halt when I heard the beep of o card key in the door and the door open and then close. I strained to hear anything but could sense someone in the room moving towards me. I heard the sound of a glass being set down and then heard what sounded like a phone taking a picture. Next I could feel some one close and then a I caught a scent of unmistakably male cologne. Damn Damn Damn I screamed in my head and began to squirm.
He pulled the note from the leg of my panties. I heard him unfold it and then another picture and another. Suddenly I felt fingers grip the waistband of my panties and roughly pull them down as far as they would go which was not very far because my legs were spread so far. It felt like he was wearing leather gloves as he roughly spread my ass cheeks and then reached between my legs and briefly fondled and inspected my chastity, a few more clicks of the shutter.
Then I heard the clanking of a belt buckle and the rustling of clothing. Now I was scared and began to squirm in vigorously. I heard the tearing of a condom package. I jumped as the cool lube hit my ass and began running down my crack and he began to rub his now firm cock along my ass crack bringing the head to rest right on my now clenched hole. He began to work the head in and I must have mentally resigned myself to the situation and relaxed a little because suddenly the head slipped in and he began to rhythmically slide in and out deeper each time until he had his entire length in me. He did not seem terribly big or even all that hard but the only reference I have is Mistress’s strap - ons. He began to thrust faster and harder I found myself rocking in my bonds to meet his thrusts and my cock straining more in its cage. I kept thinking how could I be enjoying this. Suddenly without warning he grabbed my hips very roughly and pulled himself deep into me and held there for a few moments and relaxing and releasing his grip on me. He just stood there for a few moments without moving the slowly with withdrew his cock from my ass. As he pulled out I could feel the condom stay in my ass. I thought how humiliating is this dressed like a woman, tied down, ass fucked by a stranger and a cum filled used condom hanging out of my ass. Humiliation is a big part of our relationship but this was by far the worst or best by far. Then to top it off the click of the shutter again.
I lay there perfectly still and surprisingly frustrated and feeling unfulfilled. I could hear him pull his pants up and then the door closing behind him. I just laid there tiring to come to grips with what just happened when I heard the door open again. I froze. Suddenly I heard Mistress say “well aren’t you a mess” “ you want loose?” I slowly nodded yes. As she untied me I could smell the cologne again very faintly. I began to panic a little thinking she brought him back or was she there the whole time and he came back? I didn’t even know at this point.
I finished undoing my bonds and turned around to see Mistress sitting in the chair with a huge smile. I noticed she was now wearing slacks and a plain white shirt. The pants were undone and she had a strap on cock between her legs. I must have looked completely confused. She told me to pour us a drink that I had earned it and began to explain her very elaborate rouse. Mistress had two rooms and simply left and changed, got her new strap on and sprayed herself with men’s cologne and came back and used me. Still looking at her in wonder trying to decide whether to be pissed, relieved or disappointed. She told me that her whole plan hinged on my anxiety level causing me to miss details that would betray her. And it worked perfectly. We talked about it in depth and she said at least now she knows my ass can be taken. In retrospect I have no idea how I could not have known it was not a man, regardless Mistress has taken her creativity to a whole new level.