Some of this story is true, some just hasn't happened . . . yet!
My wife, Dana, and I have been experimenting with bondage and other kinky activities for a year or two now. She is not interested in being the submissive/bottom, and I prefer that role. So with that decided from the beginning we have slowly added more and more to our list.
I have fantasized about all kinds of things for some time, but was hesitant to bring it up with her. Finally I did and we started with simple handcuffs and some rope bondage, and I have slowly introduced other ideas over time. To my surprise she has been very receptive of almost all of it.
The first big step was piss play. I was afraid she would just be disgusted and turned off by that and that I would never be able to experience it. But she soon began to actually enjoy pissing on me, and I modified a chair to incorporate a toilet seat to make it more comfortable for her, rather than having to squat over me. But that story is for another time.
Only recently, I showed her a video on the internet of a man being butt fucked by a woman with a strap on dildo, and casually mentioned that I would be “willing” to try that if she was interested. Again to my surprise, she was open to it. We didn’t do anything about it for a while, and hadn’t bought a harness, but I had bought a couple of dildos for her, hoping she would use them to pleasure herself while I watched, bound and gagged, and locked in a chastity device. About the same time I bought an anal hook and expressed an interest in crossdessing. She was ok with that too and I soon began buying some women’s panties, stockings, and other things.
Then one night she blind folded me and tied me face down across the coffee table and began to paddle me. The paddling was nothing new but soon I felt the new sensation of something slippery sliding between my ass cheeks. She was sticking a dildo in my ass! It hurt like hell at first but soon the pain went away and it actually started to feel good to me. She wasn’t gentle with it either, but I found that I liked the feeling of being abused that way. I soon bought a strap on harness, and a bigger dildo, and we used that a few times over the next couple of months. Then after that, for some reason, we didn’t do much of anything for a while except an occasional paddling. Even the chastity device I had bought and wore for a while was sitting in a box unused.
Then one night she told me that she had been thinking about it, and that I needed to make a choice. Either we could stop all of it forever, or I would have to become her slave, and that from now on she would have total control over me. “Think about it before you answer” she said. “I’m serious about this and you may not be ready for everything that’s going to happen”. I thought about it for a few minutes and told her that I was ready to submit to her in any way she wanted.
“Ok” she answered, “I’ll be coming up with some rules and expectations soon, and of course I can change the rules any time I like. Is that clear?” “Yeah” I said, and she immediately grabbed me by the collar and slapped me hard across the face, and said sternly while pointing her finger at me “The first rule is that you will address me as ‘Ma’am or ‘Master’. Is that clear?” “Yes Master” I responded. She then ordered me to go into the bedroom, strip totally naked, get the chastity device, a CB600S with a padlock for which only she has the key, and come back to the living room and put it on in front of her. I did as she said, and as she reached up to snap the lock shut she gave my balls a little slap from below to reinforce her dominance over me. She then had me kneel before her as she gave me instructions for the next day.
I usually get home from work a good hour before her. The next day when I got home I was to take a shower, shave my legs and underarms, and use a scented lotion that she would leave out for me. Then I was to dress in stockings, high heeled shoes, garter belt, a bra, and a short frilly dress. No panties and no chastity this time. Then I was to bring out the “Toy Box” and place it in a specified place in the living room and move the coffee table away from the sofa to the middle of the floor. She explained step by step that I was to take out two pieces of rope, handcuffs, and the leather hood that covered my eyes and had a snap on gag for my mouth. I would put the keys for the handcuffs and the key for the padlock on the hood, on a shelf, well out of reach. Then I was to turn the stereo up loud, kneel down at one end of the table and securely tie my knees to the legs of the table, secure the hood on my head with the gag in my mouth, and lock the padlock, then finally lie across the table and lock my hands to the table legs at the other end with the handcuffs.
That was a lot to do in an hour, but by the time she was due home I was clean, shaved, dressed as instructed, and helplessly bound with the music blaring, fully on display in the middle of the living room. There I waited.
It seemed like more than an hour before she came home. Though with the music playing so loud and the leather hood covering my ears, I couldn’t hear her come in. I only knew she was home when I felt her hand lift my dress, rub my ass, and give it a little slap. Then I could feel her checking to see that I was bound securely, then finally rubbing the sides of my head through the leather hood. She held my face and finally spoke. “You realize that there is no turning back now, right?” “MmHmm” I mumbled with the gag preventing any resemblance of speech. “You are so fucked!” she said with a carefree laugh. Then I could sense that she walked away. I lay there wondering what might happen next, and what she was doing. I could only hear the music, and feel the discomfort of my bindings and the light drape of my dress barely covering my ass.
After a few minutes I was shocked back to reality by the solid crack of a paddle across my ass. Then my dress was raised out of the way and draped across my lower back, followed by several more hard licks that almost brought tears to my eyes. The pain was nearly unbearable but I could only tense up and grunt through the gag. She softly rubbed the paddle on my sore ass for a moment and then it hit again. This time she must have swung it with all her strength, and laughed at me as I screamed into the gag with the shock of such a brutal attack.
Again, she left me there for several minutes. The pain from the paddling had subsided to a warm stinging sensation now, and finally I felt the cool leather of her riding crop slipping over the reddened cheeks. Soon it slapped hard onto the back of my right thigh, and then the left. Slowly she swatted again and again, carefully moving from the back to the inner parts of my legs, and occasionally my back and the sides of by torso. Then finally, and without warning, it slapped hard against the bottom side of my exposed balls, sending me once again into screaming pain. Then before I could begin to recover, another slap, and then another.
I couldn’t believe the pain she had inflicted, and she was laughing as she again walked away. I felt close to passing out and felt the wetness of tears inside the leather mask. I had asked for this, but was wondering if she might be going too far.
Masked and gagged as I was I had no way to ask her to stop. No matter my response when she asked things like “You like that don’t you?” or “Did that hurt, you little sissy bitch?” she just said “Good. You have more coming.”
After a short time of being left alone again I felt the coldness of lubricant being generously applied to the crack of my ass, and a gloved finger forcing some of it inside and loosening my hole. I knew what this meant and the finger was soon replaced with the familiar feel of a dildo being shoved fully inside my rectum in the first push. It took my breath away as it suddenly pushed so deep with no time to get used to the penetration. She held it inside me and leaned forward, reached under my chest, and twisted hard on my nipples, then let go and withdrew the dildo only to slam it hard inside me again. Then I could feel her hands bracing on the sides of my waist as she continued the brutal fucking, pounding my ass again and again for what seemed like forever.
Again I was grunting and nearly screaming with each thrust as she continued fucking me like some filthy slut in a back alley. The pain was now gone and my ass felt loose and worn. Then she slowed her pace and gave a few more hard thrusts, slamming her hips into my buttocks to ensure full penetration each time. Then finally she withdrew and walked away again.
After enough time for her to remove the strap on harness and gather herself, she came back to me and said “You are such a whore aren’t you?” “MmmHmm” I tried to respond, still tightly bound and gagged. She reached around and unsnapped the gag, and pulled it from my mouth. “What did you say? I couldn’t hear you.” “Yes” I responded weakly, finally able to speak. “Yes what? Bitch!” she said loudly. “I want to hear you say it!” “Yes! I’m a whore, Master!” I said, louder this time. “You look like a sissy too! All dressed up like a little slut, it’s no wonder you got fucked like that!” “Are you a sissy slut?” she asked. “Yes Master!” I said. “Say it all” she said. “Are you a sissy slut?” “Yes Master, I’m a sissy slut” I yelled. And she said laughing, “I can see that!” “If I let you up now, you’re going to remember your place in this house from now on aren’t you?” she asked. “Yes Master, I will.” I said.
“Good boy!” she told me, still speaking loudly over the loud music. I couldn’t believe she was putting up with that noise for so long. She leaned over and untied my legs from the table, then walked around and unlocked the handcuffs, allowing me to stand up. My knees were weak from all the abuse, and a little stiff from being in the same position for at least three hours by now. I was a little wobbly at first but it felt good to stand.
She moved me to one side of the table to which I had been bound, stood me facing in the direction of the sofa, and told me to stand still. I could hear the table being moved across the floor away from where I was standing, and then she was gone again for a few minutes. I stood there as she ordered, and waited, wondering what might be next.
Soon she returned and told me to kneel down. I did as I was told, and she told me that she was putting a plate in front of me on the floor. “Now you’re going to give me a little show.” “A show?” I asked. “I want you to masturbate, and cum on the plate in front of you. If you can get it all on the plate I’ll let you up, unlock the mask, and let you get dressed. But if you get even a drop on the floor, you’ll have to lick it all up. Is that clear?” “Yes Master” I said, with obvious hesitation. “I make the rules here. Now get started.” She said, demandingly. “Yes Master.” I said, as I raised my dress with one hand and began stroking my dick with the other.
I felt a bit embarrassed to do this in front of her, but she ordered it so I would do as I was told. And somehow, still being masked and unable to see made it easier for me to feel alone with my fantasies and soon my dick began to harden as I masturbated. I thought about all that had happened, and fantasized about what the future may bring with this new way of life, and soon I could feel an orgasm beginning. Soon the cum spurted out in three or four heavy loads and I aimed it as best I could toward the plate she had placed in front of me. I shuddered as the orgasm subsided, and carefully shook the remaining drops toward the plate.
She walked over and squatted beside me with one hand on my shoulder. “You did very well!” she said. “Almost all of it went on the plate, and it’s a huge gob too!” she added. “But I’m afraid there are a few drops on the floor.”
As I was horny and masturbating, the thought of licking up my cum didn’t seem too bad. I hoped I would get it all on the plate, but wasn’t too worried if I didn’t. But now, after such an orgasm, I was no longer horny and really didn’t want to do this. But I had agreed to do as she said and set my mind to follow through.
She grabbed the back of my hair and forced me to lean over, guiding my face to the drops on the floor. I could feel the wetness of one spot as my lips touched it and began licking it up through the mouth hole in the mask. “Get it all, pussy boy!” she said. “I don’t want any spots on my carpet!” Then she guided me to another, and one more, larger glob, making me thoroughly clean each one. When that was done she said “Good! Now finish up the rest of it on the plate.” Again she guided my face to the right spot and pushed my face down into the puddle of goo on the plate, smearing it on my lips, and I could feel that some had stuck to the outside of the mask and some had squeezed between the mask and my cheek. “Lick it up, you nasty bitch!” She said. And I proceeded to lick up all that was on the plate.
When I was done she took the plate and told me to stand up again. Then the table was once more moved to the center of the floor, this time oriented so my face would be toward the sofa, and I was told to “resume the position”. I told you that if you could get all of your little mess on the plate I would let you go.” She said. “But you missed, didn’t you?” “Yes Master” I said, as she replaced the handcuffs, and bound my legs again to the table.
There I waited once again, the stickiness of my own semen on my lips and face, and soon the music was turned down to a quieter, more normal volume. “Tell me you’re a nasty little bitch and you want more.” She said. “I’m a nasty little bitch, and I want more Master!” I said, expecting the paddling to start again.
Then to my surprise she unlocked the mask, slowly loosened the strap and the laces that held the back to a tight fit, and pulled the mask from my head. Immediately, laughter and applause broke out in the room as I squinted, opening my eyes in the bright light. The whole time five of Dana’s female friends, and two of their husbands, had been watching everything. I could see one of the girls with a video camera pointed directly at my face, recording my embarrassment and humiliation.
Dana came over and held my face toward the camera, squeezing my cheeks to make me pucker, and saying “Isn’t SHE a cute little whore?” Everyone laughed, and one of the girls said “That was the most disgusting thing I’ve ever seen Bobby” as she high fived one of the other girls. Then the laughter got louder as those two got up wearing strap on dildos, bigger than the one Dana had used. Before I could speak, Dana wrapped another gag around my mouth, the kind with a large opening that held the mouth in an open position. Once again I was bound and gagged, but this time able to see and hear. The others laughed and jeered as Dana asked, “Ready for round two, bitch?”