MistressDarkArt
Posts: 5178
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I have a peripheral boy who waits in the wings for a serious sub of mine to drop out or when I am not currently involved with an alpha. Toy is a panty slut who takes great delight in being transformed into a sissy...two characteristics I generally don't engage since I prefer males to submit as males. Yet there is something quite beguiling and winsomely simple about Toy that is hard to ignore. He is one of the very few cross-dressers I’ve seen who actually look appealing in women’s clothes. He is tall, blue-eyed with honey-colored blond hair and handsomely muscled with a lithe, gracefully athletic body and the kind of package women (and some men) only dream of. He is the toughest, most responsive sub I have handled. He takes whatever I dish out no matter the severity. He cums on command from just about any type of stimulation or from voice command alone when the planets line up, he's been teased to kingdom come, and his balls are swollen with cum like two overfilled balloons. Toy is easy; too easy to turn on, too easy to get off.
When Pet dropped out, Toy asked to be reinstated as number one sub until I could find the more geographically desirable and time-devoted sub or slave he acknowledges I deserve. With an offer like that on the table and no immediate prospects to begin training, I allowed Toy back into service. Since Toy is blessed with the ability to cum from nearly anything, I decided his education should include a section on what most women feel like when having sex from penile penetration without additional stimulation from toys, fingers, or tongues...in other words, the 'standard' way from which most of us are expected to scale great orgasmic heights.
We have a ritual. Toy stops on his way up the coast to bring me a pie. When he arrives, I collar and leash him with a chain to take him out in public. I give him the option of wearing a collar or a wrist restraint depending on where I plan on going. This time we were going to walk on the pier to enjoy the late afternoon sun and then out to dinner, so he chose his wrist. I love walking him out in public. Before we left, he tried for an hour to get the CB6k on his swollen cock with no luck and a lot of melted ice packs. Finally I conceded that we would have to try again later and I took him to the very end of the pier, far out over the blue Pacific. Enjoying the lovely breeze and beautiful ocean, I sat him down on the bench and pulled his jeans down to his ankles. He’d requested to arrive in panties and his cock simply could not stay contained. We did not speak as I held his leash in one hand and used the other to stroke his balls, cock, belly and thighs. He closed his eyes, sighing in pleasure, secure that I was keeping watch on foot traffic and would not let us get arrested. I teased him over and over using the one to ten numbering system that identifies where he is along the arousal scale.
Loathe to end the moment but getting chilly and hungry, I had him zip himself back up and we went on to dinner. I held his leash across the table and ordered for him while the waitress looked at the chain without a blink. If she had never seen something like this before, she never gave a clue that something was very different about this couple. After a lovely dinner of grilled scallops and salad Toy paid the bill and awaited instructions.
We arrived back at the lair and I hurried Toy into the kitchen. “Time to make your cleaning solution,” I told him. “This is your first time so we will keep it to 8 ounces. Even a beginner should have no problem with that. You are to mix ¼ tsp. of kosher salt with one cup of distilled water and heat it in the microwave to warm enough that your finger is comfortable in it.” I watched as he did so and then hustled him off to the bathroom, holding the measuring cup. I took out the large enema bag and Toy poured the solution into it.
“Get on the floor on all fours, ass in the air.” I slowly administered the minimal amount of liquid. He whimpered as the solution went in, but his blazing erection and the way he wiggled his butt from side to side gave him away. When all was in, I sealed him with a butt-plug and told him to hold it until I said he could expel. Making him count each strike, I spanked him until each cheek turned bright red with handprints, then called Mistress Holly, put her on speaker phone and asked her if she would like to come over and look at my slut on the floor holding an enema with a butt plug in his ass. She was busy with a friend, who heard the whole conversation but wished a happy evening to Toy and me. It wasn’t long before Toy began to complain that he couldn’t hold his solution much longer. I spanked him again, wiggling the plug here and there and told him he was almost there and to hold it.
“Mistress,” he begged, “I think I’m going to have an accident. What may Toy do to expel?”
“Sing Yankee Doodle Dandy twice, then I will allow you.” He sang, rather quickly. I left him alone in the bathroom to tidy up and heard the toilet flush and the shower running as I prepared the rest of the equipment in the lair.
When Toy emerged sparkling clean, I gave him an assignment to try again with the CB as I set him in front of a warm fire. Toy takes his tasks seriously and at long last he managed to get his generously-portioned genitalia deflated enough to partially fit in the device, yet still seemed to be coming out of it with funny angles, swellings and bulges. When at last he had it on, I took some pictures to commemorate his first time in chastity as he knelt and presented the key. It was quite secure...I tugged on it a few times to see if there was any chance of escape...alas for him, with the twist of the key in the lock which then disappeared into my pocket, there would be no escape.
I transferred him to the bedroom and further challenged his dignity by strapping a plug gag to his mouth so he would immediately begin drooling. I LOVE to watch my boys drool no matter how much they try to slurp up their saliva. I throw a towel on the floor under their chins and tell them to let it all out, don' try to hold or swallow it. It's so messy I can't help but enjoy the hell out of it. With his face gagged, I set him on all fours on the floor, a spreader bar widely separating his legs. After a gentle fingering, I mercilessly butt-hooked him and tied the hook to his collar so that if told to lower his head to the floor he would pull the butt hook uncomfortably up his sissy-hole while choking at the same time and drooling onto the floor. I positioned his body on the hardwood floor at such an angle that he was able to see himself stem to stern in the double glass sliding mirror.
A handsome boy in daily life, now he was transformed to bound, naked splendor as he began to drool in earnest, whimper at his neck/butt predicament , and began to hump the air, thighs wide from the spreader bar, seeking satisfaction from something. Through the CB he could not feel a thing. He wriggled, thrashed and pummeled the air with his hips...all for nothing. I straddled his back, holding his narrow hips still with my muscular thighs and alternately squeezing the breath from him and releasing him as he gasped for air. I gave him a choice of flogger or crop. He chose the flogger so of course I cropped him until his butt cheeks and thighs flamed bright red and welted beautifully.
"Owwww, owwww, OWWWW!!" he cried indistinctly through the gag with each stroke landing harder and harder, and I yanked his face up by his hair to see if he was actually crying. He doesn't like pain or spanking, and real tears had joined the saliva dripping off his chin. I then gave him his wish and flogged over my previous work. As a finishing touch, I played the spiky wartenberg over his welts, ball-sack and the tender skin of his hooked little sissy-hole until he whimpered in defeat. I removed the gag and tenderly wiped the tears and spit from his face with a clean, soft washcloth.
"Poor little Toy. Maybe you need some more direct stimulation. Here, let me take out the hook and strap on my nice solid cock for you. You have to stay in chastity but knowing you, a good drubbing on your prostate will get you to squirt and give you some relief. So let's see how well your Mistress can fuck my little Toy who can't get any sensation to his 'clit' while his 'pussy' is pounded. I'll tweak your nipples to give you a little extra, and I'll let you back onto my cock to take the depth and pace any way you like it."
And so he did, gimlet eyes glittering half-closed, soon shouting and panting "I'm your SLUT, Mistress, your SLUT! I'm your SLAVE, your SLUT, your TOY!" He was desperately impaling himself on my cock, seeking release through his prostate and anus, becoming more and more frustrated all the time.
"Oh, my poor Toy. You wanted to be a sissy so much, what with your panties and high heels and bras and stockings and girdles and garters and dresses. So you could be a wild, wanton slut and let strong, powerful women control your orgasms and make you do degrading things like sucking on a butt plug for a gag. Now here you are, and you are nearly senseless in your desperation; you can't feel a thing in your cock, your balls are so tight they are painful to touch, and that black invading dick you've impaled yourself on can't *quite* rub your little angled prostate to give it a good milking...it goes in straight and out straight, and your little p-spot needs a curve. Just like a woman's g-spot...in and out fucking is boring and ineffective. Most women need up and down/ round and round, with a complement of delicious clitoral caresses from fingers, tongues, vibrators, or e-stim at the same time to complete the circuit. Now you see why it is so hard for women to find release in the type of sex men usually want to give them. Well, try some more. Hump yourself on my cock and see if you can cum like that. Take your time until I know you finally get it. Your cock's in a cage and all you have is your ass and a big, straight rubber cock that may or may not slide by your p on the way in. Now bear down on my dick and DANCE!!"
In desperation Toy gyrated ‘round and ‘round the maypole; in and out, a figure 8, zig-zagging, growing ever more desperate with his newfound inability to cum. He became frantic, his hips punching air forward and grinding back into mine trying to extract more sensation from the unyielding rubber intruder. At last, gasping, he lowered his hips in defeat and sank into the slimy puddle of pre-cum that had escaped the slit in the CB to allow fluids out.
"Eat it!" I told him firmly. "This may be all you get."
"Please Mistress, what may Toy do to be allowed to cum? How may Toy please you for this privilege?”
"Why don't you snap off the condom that's been on my rubber dick in your ass, and begin to throat the clean dick. Get your lips all the way to the base of the dick and establish a rhythm...it'll push on my clit and will get me off if you use your fingers inside me as well."
I handed Toy a large rubber butt-plug with a condom on it and a bottle of lube. "You know the rules. Toy does not please Mistress or cum without something in his ass so Toy is reminded with each move who owns every bit of him. Now recite the ‘Pledge of Obedience’. "
Toy obeyed and put the plug inside himself. He knelt, his back straight, put his hand against his heart and recited from memory: “I pledge obedience to my Mistress who I willingly give complete control of my penis, my anus, my testicles, my nipples, my whole body , my orgasms and every part of me, submissive or not.” With the oath completed, I lay back against the comfortable pillows of my bed and guided him on deep-throating the rubber cock and just how and where to use his fingers. He was quite good at this. I'd taught him the proper way to suck cock during our first session.
"Are you *sure* you haven't sucked a boy?" I asked.
"No Mistress, no sucking of boys. I am here for you only."
Patiently and with great finesse, he throated the strap-on and fingered me until I had all I wanted. For this I rewarded him by unlocking the CB. His cock sprang out and instantly re-inflated.
"Be still, Toy. You are not to hump, move, or make a sound other than to ask for permission to cum. You will have a choice...you can either promise to eat it or not cum at all."
Toy has a love/hate relationship with eating his cum. He hates to do it but knows he will be allowed to cum if he promises to eat it. He is obedient and follows through every time. Every day he begs me for this privilege, saying he is ‘thirsty’. We have experimented with having him cum in a condom after which he bites the tip off and sucks it out. He has also used a funnel and prefers this method since he says the rubber of the condom ‘makes the cum taste bad, Mistress.’ There have been times I have him cum on a work table then lick it up the puddle from the cool, smooth glass.
I reached for the vibrator and held it under the ultra-sensitive frenulum of his dick. He had been denied so long it would only take a second or two. He did his best to be still and quiet but by his second breath he was haltingly, gaspingly asking for permission.
"Yes, Toy, in your hand. That’s my good boy. Now lick it up off your palm and fingers. Swallow all of it. Think of it as doing your part to recycle."
"I don't want to do it now," he complained.
I frowned at him. "Remember you are not to use the word 'I'. Be obedient or there will not be another time."
"Yes, Mistress, understood. Toy will eat his cum, Mistress."
And with a tortured look on his beautiful face in the candlelight, he devoured every drop.
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Toy Learns A Woman's Lesson - 
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