Letter From Ravenswood Bluff

Dear Shoeblossom:

Brinker stands, a foot precariously on each chair with his hands behind his head, like an arrestee. I shake my auburn hair and wave my double D's at him, well displayed in the bikini top, blue with sailboats.

"All I'm saying, Jessamyn, is that it wouldn't hurt to ask Shoeblossom. He's great about answering letters in my magazine, and he's a professional. He would know how long I'm supposed to be kept in chastity. I'm a healthy guy. I need more—sex, more releases."

I smile at him and finger one of my auburn locks. I peek my tongue out at Brinker, and he smiles involuntarily. But then I pick up the umbrella I got from the corner, a long black thing, can't imagine who left it—and I whack Brinker's hard cock. I whack it HARD.

"Brinker, who are you to say that you should decide when your orgasms are to happen? I've never heard of anything so audacious." WHACK! Again the umbrella comes down on Brinker's dick, and it threatens to open. Then, just for fun, I use the sharp end and poke Brinker's testicles, and he almost falls off the chairs. Careful.

I step back and pick up a box of Lucifer matches, I strike one, it's a long, wooden thing, and I flick it at Brinker's chest. He winces as it grazes his right nipple. "You're so goddamned arrogant, Brinker. And all you seem to think about is when you're going to get to squirt that thing—to stick it in me."

"B-but you have sex all the time. When I came home from Pakistan, you hadn't even bothered to tell your boyfriend to leave first! And I'd called you from the damn airport, Jessamyn. And there the bastard is, wearing my robe and drinking my Canadian Club."

"Yeah, that's right, Brinker. Felipe was horrified when he discovered what a cheap bastard you are when it comes to liquor." I flick another match, and this time it bounces off Brinker's cock. He yips like a little girl, but I must give him credit—he never moves from his position on the chairs, and he never takes his hands from behind his head. I've trained him well.

Brinker looked a bit sad, and so I lay down the matches and came up close to him, pushing my bikini breasts against his stomach as I stroked his hard cock. He's been pestering me for a WHILE to write to you, Shoeblossom. I've always felt that he would appreciate me more, if I let him fuck me less, don't you think?

Brinker breathes through his nose as he watches me stroke and massage his hard dick. It is difficult for him, especially when he calls me from the motels and hotels, and I'm being fucked by his pool boy...and I pant as I talk to him—oh, he must be enraged.

"Hello (pant) Brinker—Enrique is here (pant) just giving me a little (oh) pick me up (pant) how are you doing? God, he's got a big dick!"

Brinker's dick is fairly big, but I stopped letting him use it on me much about six weeks into our relationship. Every now and then, maybe once every two months or so, I have mercy. He loves it, mounting me, and all the grunting, and that sort of thing. Kissing my big boobs!

Normally, I only let him lick me down below, and I tease him with my boobs. After all, I don't need a naughty boy slobbering all over me! My friends who know of this relationship tell me I should be appreciative of a man who keeps me in such style, but I want him to really, REALLY want me.

Because Brinker used to discard women like cigarette butts. Four marriages, various pregnant waitresses and secretaries...he just needed someone to make him understand that she was damned important.

Now, I stroke Brinker's sweltering cock, grazing it gently with my French manicure, and kiss the tip, which makes his thighs quiver dangerously. He's such a child! And he wants you to answer his chastity belt question, and tell me that I have to respect his "boundaries"

Boundaries? Is he serious? He wants to wear the belt now and then, and PRETEND to be in chastity? I don't think so.

I am indeed a kept kitten. Brinker does something complicated with the aerospace industry. Much of the time, Brinker is on the road, and he calls me his "acquisition". Unless he goes someplace interesting, like Biarritz or Prague, I generally stay home where I'm entertained by whatever I can catch in pants.

Brinker is about six feet tall, handsome, with silver hair. His lower jaw is like the size of an anvil or something. And yes, Brinker is my chastity slave. How else could we have it? He's gone all the time, trotting the globe, and I can't have him picking up diseases in every port!

When he's at home, Brinker is locked in a steel tube, with tiny needles so he doesn't get too excited (it's irritating) and when he's flying around, he wears a plastic tube, so as to not upset the security alarms.

Brinker could easily break off the plastic device, but if I found out, I'd cut up rusty, as my British father used to say. Brinker hates to have his dignity impugned, and being taken out in the back yard of his estate to be flogged while he's stark naked is no picnic. Most of our servants understand the arrangement, don't get me wrong.

Seeing the man of the house wandering disconsolately around nude except for the chastity tube, watching me thrash him in the sitting room with my trusty bath brush as he screams and kicks his legs would give even the stupidest menial an idea of how the land lays, or the lay of the land, or however you put it. I'm not any brain trust myself, but Brinker showed me his cute little websites and BDSM magazines a loon time ago, and I'm in the catbird seat, right?

"Why do you want to be so free?" I demand as my fingers tickle the bloated veins on his hard cock. "I bet you'd like to fuck all those hos—those stewardesses, the barmaids...I know you. Filthy body, filthy mind. And you're always working out in hotel gyms, and I know you're such a goddamned charmer, Brinker.

He looks guilty. Actually, if he really wanted this, we could break it off. He has given me so many gifts, and I could go my own way...but he's fascinated by me, somehow. Who knows why? I'm just a nice kid who used to be his copy aide...that's right, I was a Xerox girl. I can't type to save my life, and Brinker needed lots of that done.

And then one day I was in Brinker's office and saw his copy of "Pain Shack" magazine, and when he came in, I had his copies, with the magazine on top. I was just a kid then, and a little worried he might fire me. But his reaction was rather amusing.

American men always get all sweaty and apologetic OR officious and demanding when they're caught doing something peculiar. Something the golfing buddies at the country club would look askance at. Why? I don't know. I was raised in Europe, where people are so much more relaxed about sex.

Brinker handled it much more maturely. I was truly surprised. "I know you must've found this magazine, Jessamyn, and it may have disturbed you." He said this so earnestly, as he brought me some Earl Grey tea on the couch. He has a big-ass office, and it's got a freakin' couch. The office is actually bigger than the studio apartment I was sharing with my sister before acquiring Brinker. How fair is that?

He gave me all this shit about progressive thinking, and asked me to be "discreet" about his interests here at the office, and told me what a sensitive feminist he was, all the time he was trying to get a look at my panties under my skirt, the son of a bitch. Men are like, confused cobras—they want to strike, but just kind of wriggle.

So I, like looked at him semi passionately, and I said something like "Oh, Mister Baines (That's his name, Brinker Caldwell Baines the Third). "I'm so excited by your magazine, I want to give you a blowjob, and I hope you don't think I'm too forward."

Once the bastard's dick was out, I grabbed a stone paperweight from his desk and mashed it on the coffee table, and Brink burst into tears. Then I slammed it again, and I picked up a sharp letter opener, running it up and down his shaft (for of course he was even more excited now, right?)

"You're such a hypocrite, you make me ill." I said to poor Brinker. I poked the letter opener into his balls a little bit, and then smiled evilly. "What people like you are like makes me sick...but maybe I'll let you off."

Then I pulled my skirt up and my panties down, and let him fuck me, and after work, we went to his place and made love for about seventy-two hours straight. He called in sick for both of us. And then he called in sick for me permanently...I get my salary, like a disability check that comes to the house or something. But I don't have to go nowhere.

At first I let Brink fuck me a lot, and then I cut him down—and THEN I noticed how much attention he gave to the chastity device pages, so I asked him about it, and he was very excited. Yeah, he wanted one bad. Till I locked it on him, then it became an "issue".

Brink's one of those dudes, the Alpha types who like to be in charge. Tell everyone else what to do, get as much snatch as he can catch, all that kind of thing. He's also a compulsive masturbator.

Dig it—instead of jerking off and dreaming of being put in chastity, you GET put in chastity, and like Aesop said, we would indeed be sorry if all our wishes were gratified, right? It's a tough compromise for poor Brink, though.

I admit, he's tried hard to bring me around to his way of thinking. He believes there should be a system—I should let him cum once a week, maybe jerking off, and then once a month I should let him fuck me. And then he'll "allow" me to have my dalliances.

I prefer the plan where he cums when I think he should—which might not be very often. I enjoy keeping the guy on his toes, and he really is much more dedicated to me that way. It's wonderful having a brilliant, older , compassionate man devoted to me, and I think subconsciously, or perhaps not even that subconsciously, he likes being kept off balance.

But then I catch him...I see where he's been trying different keys in his chastity lock, and it's so damned disappointing. One night last month I was so angry—I felt so betrayed! The belt was tampered with, there were porn magazines under the bed—and I was furious.

"Really, it's all circumstantial" Brinker protested, but I would have none of it.

"Take your clothes off and lie on your back on the bed—that's right, I'm going to cuff your hands above your head, and we're going to show your dick why "he" shouldn't tempt you like this." I said grimly. I took a hickory switch off the dresser—it had been in the bathtub all night, getting nice and wet, and I took a whack at his dick.

He moaned, gritting his teeth as the switch snapped on his glans. Brink moaned, and tried to pull away from his bonds, but he was quite securely locked down. I brought down the switch down again, in the middle of his shaft, and he howled in acute agony.

"I keep telling you, Brinker, it's up to me to arrange your orgasms for you. You are a poor scheduler of that sort of thing. Your deal is rockets and stuff. Not when you should be masturbating." WHACK! SMACK! "I know that you are really aroused, especially by looking at yours truly, eh?"

I opened my robe slightly so Brink could see the swell of my cleavage. I licked my lips at him, and he stared at me with just the most intense desire. I knew if he opened his mouth he would probably proposition me, and that couldn't happen...bad boy!

I lifted the switch again. WHACK! SMACK! CRACK! Tears came coursing out of Brinker's eyes, and he began wriggling again on the bed, trying to get out of it. SNAP! The switch bounced off Brink's left nipple, and he screamed again.

"Honey bear, I love you so, but you're not a man. You're just a subbie. I need guys to fuck me, fuck me HARD, and you just need to do what I tell you to." I dropped the switch and climbed onto the bed, now stark naked. I rubbed my clitty across Brink's hard cock.

Baaack and fooorth, gliding it up and down. "You like having a taste of my pussy don't you, Brinker?" I lifted my hips and lowered my buttocks onto Brink's swelling cock, covering the head. "You didn't know I had such a wide asshole did you babe? That's right, I let the boys ram it up there, too."

Fresh tears sprung in Brinker's eyes. He knew that he would never, never get to do me there, and would have precious little more future experience in the initial hole, either. There would be a long restriction. I dropped onto his cock with my pussy hole, teasing the tip with my slit.

Brink began panting and gasping, hoping against hope that I might keep my pussy on his cock long enough to let him release. But I knew him too well. I slid up and down tantalizingly, four or five times, watching him gasp and moan, and then I jumped up again, pulling myself off the bed.

I took my bullwhip off the wall and I cracked it, letting the tip loop around his hard cock. Brinker screamed, and his cock wilted just a bit. Then I cracked the whip onto his balls, and he let out a bellow like a hog being slaughtered.

I have quite a bit of practice with the bullwhip, and cracked each of Brink's nipples, and then cracked him again on the chin. "Please, please...you're going to kill me, you'll put an eye out." But I wouldn't do that! I just wanted to lay some streaks on him...and they came!

The bullwhip hit his stomach, his legs, and his inner thighs, under his arms and on his elbows. I flipped him over, and covered his back, buttocks and upper thighs before I was through. I noted that Brink's nutsack was hanging out and gave that just a couple of licks as well.

Finally I untied him, and asked if he would be willing to put on the chastity belt again and try to stay honorable. Could that be a possibility, or would we have to do more bullwhip work?

Poor Brink, he was covered with red, bloody marks and then, for hygiene reasons, I threw a bottle of rubbing alcohol over him, and he was in slightly more pain...but you know, I can't risk him getting infection.

He just shook with terror, and then he nodded. He said sincerely. "I love you, Jess, honey, and I want, and need a chastity agreement, but I-I need more orgasms, and I can't take another punishment like this one." Brink paused. "Can we find someone—a disinterested party to decide this one?"

And that's of course why I've gotten a letter out to you, Shoeblossom...you're the one who we want to tell us—should we use his plan or mine? I think it's ridiculous that a slug gets any decision at all, but on the other hand, he's been very generous to me, and I love the guy. Do you have any ideas about this?

Thanks,

Jessamyn Hedley and Brinker Baines

Dear Jess:

I have little hands-on experience in the BDSM world. I originally started out running a hardware tips column, and then there was some sort of postal mishap and then I started getting these BDSM letters. If it weren't for the $250 "reading fee" I charge, I wouldn't answer them at all, and of course I have little experience.

That's why so many of my replies are um, somewhat bland. I think most of you people are insane. However, I have my duty to do, and so I asked others who've more experience than I. (But you still must pay me.)

Donna B. of Bangor, Maine says—"My husband, Fabian, also objects to unlimited chastity time. He wants something to look forward to...that's understandable. So I let him know that one night during a two month period—I don't let him know when—he will be allowed to orgasm, while I put his belt in the dishwasher. I'm not naturally cruel, and I think it's only decent."

Ronald I. of Tomales Bay, California tells me "My wife and I have been practicing chastity and denial for twenty-two years, and for the past seventeen, I've been allowed to jerk off on New Year's Eve and the Fourth of July. I had more frequent orgasms previous to this, but Oleander became quite annoyed when I had similar demands that Brinker has, and said these would be my two definite orgasms. I regret it, but at least I know when they are."

Anatole V. of Boylestown. Pennsylvania says I should offer you, Jessamyn, HIS number. Anatole is not as prosperous as your friend Brinker, but he owns a fairly respectable pizza parlor, and is dying for someone cute to control his orgasms. He says you can do whatever you want to him!

Brooke H. of Easton, Maryland says that she believes that orgasms should be based on perfect behavior. Her boyfriend has to sign in when he comes home from work—no nights out with the boys—and he has lots of chores to do, that whole route. Theoretically, he is allowed to cum every two weeks, but he gets three days for every offense, and so he averages orgasm about every three to four months. She thinks Brinker is spoiled and self-indulgent...

Shaun B. of Baton Rouge, LA thinks that Brinker is spoiled as well. Shaun is on a key holder plan with some woman in Eastern Europe, he's never met her (could it not be a woman?) and he must pay her one hundred dollars every time he gets the key...and he must mail it back within 24 hours, she checks the date. As Shaun makes about $400 a week at the 7-Eleven convenience store, his orgasms are rare and "much appreciated" Thanks, Shaun!

Squirmy and Tallulah C. of Charlottesville, Virginia are both in chastity, and are enslaved, apparently by their cleaning woman, who unlocks them once a month after they completely scrub their house spotless and then pay her. The cleaning lady, Juana R. loves her work, and says America is everything they ever told her back home.

Foster D. of (address deleted by request) tells me that he is in chastity for two months at a time, and generally is allowed to masturbate into a glass of Ovaltine and drink it by his grandmother before being re-locked if his grades are good...but since Granny had her stroke, she can't remember where the key is, so stuff's been confusing...he is hoping the key is in the garage somewhere, and wishes Brinker luck.

Lady Henriade, of midtown Manhattan believes that orgasms, like allowances for lazy offspring, do little for the receiver...she is reluctant, but she will allow occasional orgasms for the eleven slaves that reside in her house in exchange for heavy tips, and of course while they're jerking their willies, she is whipping them with canes and sticks and whatever. She says it takes the power out of the release...and then she wrote something to me about "ruined orgasms" but I have decided not to put that down here.

So I don't know what to tell you kids. Brinker sounds like a nervous wreck, though—I think you have a nice little moneymaking thing going on there, and if you can fuck half the East Coast while he's on trips, you might let him self-abuse once a week or so. But I'm not an expert. They just seem to think I am here!

Best, Shoeblossom