Letter from Vines Village

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The story of Mistress Gertrude.
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I drive a sterilized knitting needle through my son's left nipple. Sowell grimaces, but he is sucking on one of my bloody tampons, and his buttocks hurt from the vicious caning I gave him earlier.

I surprise Sowell—when he's coming out of the tub, wet, naked and vulnerable, I charge in with my whippy cane and leave red, bloody streaks all over his slim white body...and then of course I drag him out and began torturing his nipples...what a joy being a Mommie is!

Sowell's younger brother Seward is upstairs, cuffed to the radiator in the bathroom. He is in an adult diaper (Seward is 18 and Sowell 21) and is trying desperately not to soil it, because then there will be cane action from Momma there as well!

My daughters Marilyn and Victorine run a keyholder service—many of the single submissive men in the Vines County area. A typical client is Mr. Tegaleaze, whose dominant wife died some years ago. After a time out of chastity, Teg realized that he was spending so much time chasing bimbos that he was neglecting his career, and he came to my beautiful Victorine, a saucy and quite curvy redhead, for assistance.

Vicki put Teg in a locked chastity device, and once a week, for a fee of $350, Teg comes to see Vicki, and he is quite horny and almost beside himself with desire. Vicki greets him in a babydoll teddy, usually powder blue (that color, the fabric pulled snugly around Vicki's generous cleavage sets poor Teg off incredibly.)

First Vicki orders Teg to strip and hooks his wrists to a ceiling appendage, and then she unlocks his chastity device, and washes and then strokes his penis with her long purple nails. She knows how to make him extremely addled with her teasing, and sometimes she even rubs the tips of her beautiful breasts, or her curvy buttocks against his penis until it is ready for a nuclear explosion!

Vicki will go over Teg's sales reports for the company he works for, see how many paper cups he is hawking on his rounds, and if he is short a certain amount, If he's short, Vicki will get a straightened coat hanger, or a fiberglass riding crop and whip Teg's penis until he is weeping in just intense pain, before stroking him to hardness again.

She also will go around to the back and thrash Teg's back, buttocks and thighs with a blacksnake whip, making him dance miserably...

But, when Teg has done a good job at work, Victorine will stroke Teg's penis for nearly an hour before stopping, just before he achieves orgasm, and then lock him back up again.

She then checks off a box on a record she has. If Teg can make good sales records for four weeks in a row, she allows him to jerk off into a little cup in front of her, while kneeling...it would seem that if Teg worked hard, he could get one orgasm a month! But of course there has been a recession, so Teg's numbers have been down, and in the sixteen months he has been seeing my lovely daughter, he has only cum five times!

My third son, 19 year old Pollard is at a rock concert a rare privilege—but he's sucking cocks for small change behind the Jiffy-Johns. If Pol can raise five hundred dollars, Mummie may give him the key to his chastity belt back before Christmas!

My twentysomething stepsons from my husband's first marriage live with us too—Towlen Jr., called TJ, must visit Master Rex in a distant county once a month to "earn" his masturbation privileges, as Rex has the key to the chastity belt, and puts poor TJ through a series of tests involving pain tolerance and fellatio practice...

And Spofford, TJ's younger brother is a systems engineer, and can do his entire job with a laptop, so I keep Spoff in a cage in the cellar, just big enough for him and his computer...and the paychecks come to me!

The Cippolone brothers, Desederio and Ambrosio, are refinishing the cellar into a basement recreation room, and they take turns peeing into Spoff's mouth as he crouches in his cage to keep him "fresh." (Also, the cellar has no bathroom, and Spoff, in addition to taking the Cippolone's urine, must defecate and urinate into a bowl and consume it before I come to hose him down every night.)

Sometimes I send Spoff downtown to the Peep Shop, a peep-show place where guys jerk off in booths watching girls dance on the other side of the glass—you know, ordering the girls to masturbate themselves, etc...and they jerk off all over the booths...

But the Peep Shop doesn't need janitors to clean up all the semen the guys leave, because I have my sons rotate in turn and go down and lick up the floors and the glass walls with their tongues...my little Semen Demons do such good, hygienic work getting rid of all the used sperm mess from the various citizenry of Vines Village!

The boys can thank their strict upbringing to their father, my husband Towlen O'Toole, Towlen had fantasies of submission and introduced them to me, an innocent bride, just in the first few months of our marriage.

I first heard about BDSM on my dates with Towlen...his brother Traddles had been in a femdom marriage, and then after the divorce,

Traddles's ex-wife had kept Trad in a chastity belt, forcing him to come visit her (bearing cash) to get a chance to be released for masturbation...but according to Towlen, often Traddles was just penis caned and re-locked up and sent home, weeping. But he always went back.

"That's so weird" I protested. "Why doesn't he just get some pliers and rip off the chastity belt?" Towlen just grinned at me.

And then, when I discovered that Towlen wanted his own penis locked up, I was utterly dumbfounded. Sure, I could give him a few bare-bottom spankings, a little teasing, why not. He was a good husband...if a little perverted. But to lock up his junk? C'mon!

But then Towlen suggested I talk to his brother Traddles's ex-wife, Rethea. I was a little nervous, but finally I called her, and Rethea arranged that we have lunch at her house, and amazingly, there was Traddles, naked, except for an apron, serving up the scones and scrambled eggs and tea, and Milos, Rethea's current husband was tea-ing with us, fully clothed....

And believe you me, there was more than one difference between the two husbands. Traddles was pudgy and bespectacled, and had lost most of his kinky hair...Milos was a handsome Greek...yes, quite easy on the eyes!

"It was really interesting, Gertie, "Rethea said, as she held her cup out to be filled with Earl Grey. "I was quite amazed when Trad asked me to dominate him when we first married in '73m but by 1980, I'd gotten quite used to having this servile, cunt-lapping human bank account looking after me."

Traddles spilled a bit of tea on the tablecloth, and Rethea smiled grimly. "Excuse me, Gertrude" She got up as Traddles moved back, apologizing, his clothespinned nipples bouncing above the apron.

"Over the couch, fat boy!" Rethea was quite intense...she had platinum blonde curls, and a great figure, and was dressed in a snug white top and tight jeans and high heeled pumps. She ripped off Traddles's apron, leaving him naked except for a chastity belt and the nipple clamps, and dragged him over the sofa arm by the ear, and crooked her finger at Milos, who handed her his heavy leather belt.

I was shocked at how hard the whipping was...Traddles bounced and screamed as he lay across the chair arm, and Rethea swung the belt, buckle first, and laid quite a latticework of searing red marks on his corpulent bottom.

Finally, Rethea gave Milos back his belt. "You are a clumsy and pathetic servant, Traddles!" At this point, Traddles was just kneeling naked on the floor, weeping bitterly.

"It's amazing, Gert." Rethea said as she sat down next to me again. "I've trained him for years, but he's still such a fuck-up. But to finish my story. Part of my domming Traddles when we were married consisted of taking lovers, while, of course he was locked in that cute little doodad you saw on his penis."

Milos laughed loudly as he watched Traddles rise and tie the apron on again. It was such a contrast, remarkable, really.

"But after years of taking lovers, I began fooling around with Milos, who was a worker in one of the warehouses in the company Traddles owned, and I realized I was in love with him...so I divorced Trad, but I let him come back a few times a week to clean the house, give us a little cash, and take the discipline he so truly needs."

"But Rethea that seems so unfair." I protested. "You still have Traddles locked up, even though you've divorced him and are married to someone else? He can't have the opportunity to date other women?"

Rethea laughed shortly. "Look, Gertrude, If Traddles said the word, I'd unlock the belt and send him on his merry way. Legally, I have no hold on him, especially now that I have married another. But Trad loves his Mommy, and likes earning his orgasms."

Rethea patted Traddles's buttocks affectionately as he brought back another plate of scones and he smiled at her adoringly. Milos coughed and regarded Traddles contemptuously as he puffed his Marlboro cigarette, and then, to my revulsion, he snapped his fingers, and Traddles got on his knees next to Milos's chair, and opened his mouth and yes, Milos tapped the ashes into Trad's mouth.

"Yes, I find ashtrays on a table so ugly." Rethea said, watching my nauseated face. "But anyway, Traddles was brokenhearted when I announced the marriage was over, and after he begged me to continue his chastity training, I thought, hey...why not?"

Rethea laughed. "After all, when Traddles had been living with me, I'd locked him in the belt, at his request, and we'd started out keeping him locked up for a week or two at a time, to see how it went, him getting to fuck me after seven long days of chastity..."

I looked over at Traddles's cock bulging against the chastity cage. It looked almost purple. Then to torture him a bit while his ex-wife Rethea was talking, I opened my shirt and flashed my cleavage, just for fun!

Rethea continued. "And then after I got more into dating cute boys, I just let poor Traddles jerk off...and then I extended the time between orgasms...until it was about once a month...so once a month I still let him out, and Traddles lives in a little apartment across town, Milos and I have this big house...and Trad is our bankroll and, astonishingly our maid!"

Milos interrupted, in his thick Greek accent. "Traddles is pathetic loser, sad."

Rethea grinned. "And sometimes I let Traddles service us in bed, sucking Milos's balls while he fucks me, or licking up all the spermy mess. It's good for Traddles, and having him bring us drinks after the whole sex thing is just wonderful, you know?"

Rethea motioned Traddles over, and ordered him to put his hands behind his head. As I watched, Rethea took a key from her pocket and unlocked the chastity device, and released Traddles's short but bulging cock, and she began playing with it casually with her silver painted, sharp nails.

"It's so amusing to watch poor Traddles...he's so damn frustrated. And he does stupid shit like go to stripper bars at night and let them lap-dance him...but he's all locked up which makes him even more frustrated." Rethea laughed...

Rethea ran her long slim fingers over Traddles' cock and he got harder and harder. Milos leaned over, and to my horror, he butted out his cigarette on the head of Trad's penis, and then popped the butt in Traddles's mouth, and it didn't seem to faze Traddles at all!

Rethea began toying with Traddles's swollen balls. "Sometimes Traddles will call me at night and beg me to let him come over and be unlocked, the frustration is too much. I'll be laughing at him as Milos is fucking me to endless orgasms...but I tell him to be patient. But he's happy, aren't you Trad?"

Traddles spoke finally. "Yes, Mistress Rethea. I have intense desires to cum, but my need to serve you and Master Milos is much more, and I know if I work hard I'll get an orgasm, although last month you denied me because you felt I'd been shirking my duties."

Traddles breathed deeply as Rethea continued to stroke his cock slowly, and we all watched as he shook in a pre-orgasm. I wondered if he'd cum all over the table...but then I noticed that Rethea slowed down her massage of his bulging, tumescent penis, just enough so he didn't go over the edge.

Traddles smiled at me. "Miss Gertrude, I hope you do marry my brother. He and I were raised by a very strict Mother, and unfortunately we are forever hard core masochists...and it's hard for a submissive man to find a woman who understands."

Traddles looked adoringly at Rethea. "I am so happy with my darling Mistress, even though I don't see her as much as I'd like. The whippings, teasing and torture are just what I must suffer as my due for serving my darling, and of course Master Milos."

Rethea laughed and reached up and tweaked Traddles's right clothespinned nipple hard, and then squeezed his nuts until he nearly bent over...and then as I watched she locked him back up.

"I felt the pre-cum, horny boy, and none of us want a mess."

So I had that conversation with Rethea and Traddles shortly after my marriage to Towlen back in 1984, and in the past twenty-six years, life has been quite the adventure!

I began giving Tow long, sensual teases, tying him naked to the bed and dressing up in a leather jacket, tight top and faded jeans, and rubbing my long painted nails up and down his stiffening member until he was begging me for a release...and then I'd lock him up for a week, in a tight little chastity belt, and then do it again!

Watching Tow's balls become burgundy and then purple was incredibly entertaining for me, and it made me laugh when he teared up and begged for just a little teensy squirtie...but of course I wouldn't give it to him!

And then came the caning. Tow would stand or kneel on a hassock, his unrelieved cock sticking out and I'd raise the cane...WHACK! WHACK! It was comical to watch him topple over, grabbing his poor penis in acute pain, and of course since I'd ordered him to hold his hands behind his head, I'd become enraged and begin whipping his prone, naked form as he wriggled about on the floor.

I began caning Tow's cock in 1984, and by 1985, maybe March of '85, Tow was able to stand still, gritting his teeth for about ten whacks across his suffering glans before collapsing. Sometimes I'd run my manicured nails up and down his cock when I'd whacked it into tiny-ness, and it would re-erect and I'd give him another ten slashes.

By 1990, I had a boyfriend, Anson, who would cane Towlen's penis also, hitting it much harder, and by the mid 90's, I'd bring home various bar pick-ups, promising them excellent fellatio if they'd give my poor hubby's pee-pee a good slamming.

Towlen could have left at any time—but he was so captivated by his chastity, and the longer he was locked up, and his cock was regularly punished, the more he was obsessed with my body. He didn't see me in the nude very often, usually he was naked and I clothed, even when the kids were growing up...but I wore very revealing outfits, and he cried in misery (mixed with desire) for my body.

Once a month or every six weeks, depending on his good behavior, I would allow Towlen to masturbate into a pair of my used panties, and then suck them dry of his semen...he looked so ridiculous with wet underwear in his mouth!

And yes, Cheryl Hynes and Lauren Fenwick are coming over to assist me with the Vines Lutheran Redeemer Church Preschool Rummage sale—I know you like those girls, and they will probably ask why your bare buttocks are hanging out, and why poor Traddles is polishing the silver in fishnet stockings, and I'll have to just explain that my boys are onanists...how sad."

Traddles and Towlen's Mother began trying to discipline them after they both turned 18....

But there was no reforming the masturbation habit. Towlen said even after he'd spend hours kneeling or standing in the corner, using perfect posture (Mother would put books on his head and a glass of wine on the top of the books, and if one drop was spilt—all hell broke loose) standing there with the rat trap on his penis and two more pinching his nipples...he still played with his nasty thing!

Mother would tie Towlen to the bed, and splice a lamp cord and run the electrical sparking thing over Tow's naughty penis, burning it in places, but let's face it, a testosterone filled youngster is just thinking about sex all the time!

Sometimes Mother would bind Traddles and Towlen's hands in sandpaper gloves—she'd made them herself, stitching the mittens with sandpaper from her late husband's workshop...and that might help for a while. To make sure the cure worked all the time, the boys would have to go to school wearing the gloves, and of course everyone knew why they were wearing them...and there was a bit of uh, teasing.

After Towlen and Traddles graduated from high school, they lived at home and went to Vines State—after all, she didn't want the boys to fall back on their chastity regimen by attending some sexy college elsewhere. This was especially heartbreaking for Towlen, who had gotten into Harvard, Princeton, Yale and Swarthmore....but Mother wouldn't let them leave town!

Yes, Mother O'Toole raised two excellent citizens, and then I inherited one of them. I have really tried to be strict with Towlen, and of course I raised my children in the same strict way.

I didn't want my sons to be getting bad messages by being too independent with friends and social life, and so when they started elementary school, I sent them off in frilly dresses and sailor suits and they were taunted so unmercifully that they ran home to Mommy right after school, and of course came home for lunch every day so they wouldn't roll about with the roughnecks at recess!

Shoeblossom, I just wanted to let you know that an old fashioned dominant wife and mother is doing her duty here in the heartlands!

Best,

Gertrude O'Toole

Dear Gertrude,

You certainly have the bases covered! Hope that things continue to go well for the O'Toole family!

Shoeblossom

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3 Comments
bonnietaylor2bonnietaylor2over 8 years ago
Here;s why annony is a pure asshole

You see his wife left him after cheating on him for years. She told me his dick was 3 inches hard and he never satisfied her. So mow he goes insane when a LW story doesn't kill the wife. If he keeps this up this site will have no good writers left!!

AnonymousAnonymousover 8 years ago
Stop posting this drivel

You can't write

slaveboy6slaveboy6over 8 years ago
Excellent

Great letter, it sure got me hard...i'd love to be caned by Mistress Gertrude

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