Letter from Vancouver

And then I have other troubled men in need of supervision.

Myron Caxley is a 23 year old man who lives about a mile from me. I met him through a personals online chat group, and we have been having a thing for about three years. Like Conrad, he is rich and spoiled, and is absolutely fascinated by his orgasms being monitored.

My mother toiled in one of Myron's father's dry cleaning emporiums, and his father, Cicero Caxley was a real asshole...And, Myron's uncle, Fairacre Caxley, once called my esteemed mother a "cow". I've never mentioned this to Myron, but certainly this has fueled my intensity in his training!

Unlike Conrad, Myron has amazing musculature and not an ounce of fat. He is locked in chastity about eleven months out of the year, in four month portions, and when he is allowed to cum, he must suck his own dick! Myron is an autofellatrix, and I've met so few of them!

After we have a grueling weekly session, for which Myron reimburses me rather generously, I unlock his chastity device, and then I tease him for about an hour before instructing him to suck his own penis, his hands manacled behind his head. The number of crunches he must do to achieve this feat I can only imagine.

But, after he's sucked for a while and he's on the verge of cumming, he takes his head off his dick and asks permission, and 90 % of the time I deny it. I tap his dick into wiltedness with my wooden spoon, and then he sucks again...

Sometimes what I'll do is toss a single dice, and whatever number is on the die when I toss it, is the number of minutes that he can suck his dick, and get an orgasm out of it. Since the maximum on the die is six, that's BARELY enough time to slurp his dick into a state of orgasm

And Myron does his best, but usually fails. I also distract him while he's sucking, by tapping the back of his head, flashing my boobs and sometimes shooting vinegar into his eyes from a squirt gun.

Or, while he has his hips jacked over his head, and he's licking away at his glans, straining his neck to get the damn thing in his mouth, I'll go on the other side and stick my dildo in his butt and ram it in and out with my hand...that got him so upset once that he bit the head of his dick!

At one point, Myron was still just masturbating on a monthly schedule, and finding ways to hamper this took my full imagination. Whipping his ass while he pounded away was often fun...and I'd make him stop again and again, until he was super horny, and then I'd pull his expensive silk shirt, the one he was wearing on a hot date, in front of him, and he'd cream all over it!

And after thirty days, he'd cum like a fire extinguisher. The frustrated man fascinates me. Myron has a twin brother, Byron, who is also my slave, but lives in the U.S. Byron is kept in chastity as well, and when he comes to town, about every two months, if he qualifies for an orgasm, I have Myron suck him off, which isn't too thrilling for either of them. But getting to cum is big, right?

As I said earlier, Myron dates, he's a handsome guy, but he is very careful about not letting the date go too far. They can't get his pants off. Sometimes he can con a girl into stripping, and he keeps his shorts on, and goes down on her...but that can't get past two or three dates. They want to see the wee-wee. As a result, Myron doesn't have many long-term relationships!

And the best part of this, is Myron salts a little bit of Cicero "Chick" Caxley's filthy lucre into my pretty purse every month. And this makes up for more than a few past wrongs, eh?

My first time experimenting with BDSM was when I was a chirpy 19 year old, living in a group house in college. My best buddy, Bert was, not someone I wanted to date, but nice for a twentysomething.

I found some femdom magazines under Bert's bed. Terrible pics, terrible writing (this was way back in the early 90's, dark ages) and when Bert came into his room, I was sitting there in my short-shorts, thumbing through it, and then I looked up at him insolently.

"What the hell are you doing with that magazine, Sagesse?" Bert demanded. "Give it to me. Why are you in my room at all? Do you need some money, or to borrow my car?" He was, like I said, tough, but incredibly generous.

"What's the deal with this dude?" I asked, neatly pulling the magazine away from Bert's lunge. "He's got, what is it? Clothespins all over his body. And that woman in the hideous corset is knocking them off. Why are the pictures in black and white?"

"It is none of your fucking business, first." Bert said, as he finally pinned me down and took the periodical out of my hands. "And secondly, she looks great. And that guy is being put through a lot. It's an um, interest I have, bondage."

"You'd scream like a pig if someone knocked clothespins off your body" I said, giggling as Bert good naturedly tickled me. "I'd have to get you a bonnet and a rattle, you'd cry like a damn baby."

Bert is a big, tough man, muscle bound, and he can never back off of a dare. We went out into the woods, and he took off his shirt. "No, you take it all off. Get naked!" I ordered.

Once Bert was naked (and blushing) I used some baling wire to tie Bert's wrists to a tree branch, and then I covered his body with clothespins. Nipples (he winced) arms, underarms, stomach, cock balls, inner thighs, the whole deal.

His dick was especially difficult to do, as I had to give it a couple of licks to get it utterly hard...and then I put nine pins on, which is remarkable, as Bert, a Catholic is circumcised.

And then I walked away from him. "Where the fuck are you going?" he screamed. Of course, Bertrand didn't want to be found naked in the woods, covered with clothespins. He's shy like that.

But I leisurely walked away, waving my tight little ass at him, and found a willow tree. I took Bert's Swiss Army knife and cut a long switch, and trimmed it, listening to the poor guy's outraged screams in the background.

Then I lit a joint and smoked it, and that took another five or six minutes. And finally I returned to him.

"Now we'll see how tough you are, Bertie." I grinned at him.

"Let me go, you little bitch!" Bert was outraged that this was happening "What if Dompierre (a local farmer) came by?" He struggled, but baling wire is tight stuff.

I walked up to Bert and laughed and swung the switch, knocking off one of the pins from his forearm, and Bert winced. But he said nothing. I swung again, and got one off his stomach, and he bit his lip.

"Forget it, Sagesse, you'll never get me to moan a bit." I noticed that his dick was quite hard. I aimed and tried to knock one of the clothespins off the head of his swelling cock, and it didn't come off, so I got irritated and hit his cock again, and yes, Bertrand screamed.

"Oooh, do I hear a little girl crying for her Maman? (We were speaking in French) I held my hand delicately to my ear and rolled my eyes, and Bertrand blushed in absolute rage.

Then I leisurely knocked all the clothespins off his shoulders, neck, chest and arms, and then went for the legs. By the time I knocked the last clothespin off Bert's legs, he was weeping. For the first time since he was five, I suspect.

But I ignored that. I leaned down and stroked his cock, which still had many clothespins on it. "Poor thing. It's been tough, huh?" I gently tweaked one of the clothespins which was pinching the side of Bertrand's shaft.

Bert's face was covered in tears and shame. "I guess you learned not to doubt your baby sister, eh, Bertrand?" I asked, and he nodded. "But we have to finish the job."

And then Bert began shaking his head, but his dick was SO hard. I decided to listen to the little head. WHACK! WHACK! THWACK! SMACK! Bert's screams could be heard throughout the fortunately deserted woods.

Then I went to Bert's behind, and broke the switch on its 49th swat on his quite welted buttocks. And then I released him, a little worried that he might take revenge, though Bert had never been anything but gentle to me...

But when he was completely free, I looked up at him anxiously, and he picked me up in his arms, (I was five three to his nearly seven feet) and kissed me, and held me close in his arms, stroking my dark curls tenderly.

Bert dressed and we walked back to the house together (after cleaning up the somewhat bloody clothespins) and we didn't discuss it for several weeks. And then one day I came home from school, and he called to me from upstairs.

"Guess what I bought at the trading post?" I looked in the bedroom, and there was a short carriage whip, with an intimidating handle. "I thought it would be um, cute." Bertrand said nervously.

I walked over and picked it up, leaning so he could see my cleavage in my tank top. "This is a nice thingie." It had a nylon lash. I fingered it. "And where's my baling wire?"

"They had police handcuffs at the Trading Post too" Bert said, a little eagerly.

When we got to the woods, Bertrand stripped and I locked his hands behind his back. I shoved one of his smelly gym socks in his mouth. "We don't want people to think I'm killing a pig out here."

The carriage whip did lovely things to Bert's ass, back and lower thighs. Within fifteen minutes, he had black and blue marks, bloody lashes, and he was lying on the ground, weeping abjectly.

With typical adolescent enthusiasm, I made him roll on his back, which must've felt horrible, all the bloody welts blending in with the sharp rocks and broken glass from numerous discarded whiskey and beer bottles from the log-cutters in the forest.

I bent down and stroked Bert's cock until it was rock hard. He was terribly embarrassed, because although he'd suggested I take some of my own clothes off, I'd actually put a snug turtleneck on, because it was rather brisk on that fall day.

"What a big dick you have, Bertie darling." I rubbed it some more, my red nails blending easily with the pinkness of his cock. "But you know, big dicks aren't all they're cracked up to be. I know your girlfriend Tinette thinks this dick is hot stuff, I've heard her talk about it at the school dances...but it can't stand up to real punishment can it?"

I stood up and lifted the whip. Bert's eyes pleaded with me for mercy, but I was, as Clint Eastwood would say "fresh out". CRACK! The short carriage whip left a long red weal on Bert's still rather engorged member.

I lashed his dick again, and he howled, even around his gym sock. Now his dick was small. So I stepped out of one of my clogs and rubbed his dick with my small painted toes, and what do you know, it sprang back up again!

"What are you a degenerate?" I asked him, shaking my head. "To lust after your baby sister's toes like that. You need more punishment!"

I swung and landed the whip ten more times on Bert's dick and then kicked him in the balls. Then I picked up his clothes and walked off with them in my arms, and he had to rise, with his hands still manacled and follow me back to the house.

We did live in a rather secluded place, but people are often around. A young man, Sebastian was walking by. Bert and his friends often harassed Basty, because he was gay, although they were never violent with him.

Basty of course thought Bert hot stuff, and so when he saw poor naked, welted Bert following me with a gym sock in his mouth and his hands cuffed, he stopped and gazed.

"Basty! Would you like my friend Bertrand to suck your dick?" My first words to him, I swear. Bert shook his head violently, so I went back with the whip and made a few new scars...and within five minutes, Basty had a condom on his dick and not only did he cum in Bert's mouth, but also in his blistered ass! It was quite an afternoon!

After Bert had emptied Basty's balls for the second time, I decided it was Bert's turn, so I let him masturbate in front of us while I poked his balls with my heavy clods. I know I seem like a heartless bitch, but Bert went back to the woods that evening, and got the whip, and a couple of days later, he was knocking at my door with it!

Today Bert is president of a bank in Halifax, but he comes to visit every few months, and you've guessed it—he's in a chastity belt and I have the key! We've worked out a system where we meet at a hotel whenever he passes through, and I tease, torment and tie him up, and he gives me way good head.

Con and Bert don't get along, which is odd, since they have so much in common. But I don't have to keep my admirers apart, they never see each other. And when Con can't afford to buy me a new car, Bert does it, or Silverlode, or Myron. I'm a happy girl!

Fondly,

Sagesse

Dear Sagesse

I can't tell you how ingenious your life seems! Hope you can continue it this way. You seem appreciated, and isn't that what life's about?

Best

Shoeblossom