SLAVE GWYNETH’S DIARY

July 28

So today I was coming back from my business trip in Costigan Heights and on the highway home, I drove past a group of motorcycle guys, obvious patched bikers. I waved at one of them, and he waved back, and I pulled over, and he and the other bikers pulled up, probably quite pleased to note an attractive, curvy blonde waving them over.

I stepped out of the car, and made my pitch to the guy who I guess was the um, leader. His name was Phil. I think I might have shocked him. I told him what I needed, and told him that I would be willing to pay for it, as well as pay for the motel room, and to service him and his friends in any way they liked, after it was finished.

Phil, who was a nicer guy than he looked, which was tattooed, bald and scary, insisted I didn’t have to pay them—indeed, they’d love the opportunity! “I’ve had some rough sex.” But I told him, that it was important that I paid for my needs, that I needed it quite intensely.

Phil reminds me of my Uncle Henry, who once made me take my jeans and undies down in front of his farm hands because I accidentally killed a tomato plant when trying to hoe tomatoes for him…Uncle Henry was the first one to suggest to my parents that I keep my head shaved so I wouldn’t suffer the sin of vanity… and I remember he seriously welted my full bare bottom that day on the farm!

But I was a little nervous about these bikers. I needed a session, but not to be murdered…but you know, it’s not my choice anymore. I need to submit more than I need to breathe!

We pulled up to a real shitbag—Motel 8, or 6, or some number, and I paid for the room and invited Phil and his six friends in. They stood and looked at me for a moment, while I disrobed, taking off my Chanel skirt and jacket, unbuttoning my silk blouse  and then removing my French demi bra and panties…and then I took off my wig.

This might have staggered lesser men, a cleanly shaven head on an otherwise attractive and normal looking woman. But other than a gasp or two, they continued to just stand, dumbly.

I’ve been good about keeping my head shaved. I remember my Dad caught me getting a little fuzzy on top, and he took his carved wooden Hand of Punishment from the wall and he thrashed me over a kitchen stool for ninety minutes before hanging me by my tits from a beam in the garage. I am lucky Dad and Mother let me live at home while I was in college…they taught me so much about self-discipline!

But my head was shiny, and the gang members seemed absolutely possessed by my poise as I walked around fully naked in the motel room. I have 36DD breasts and a supple bottom, and certainly fairly long legs—so I think they were paying attention!

I went into my briefcase and took out the cuffs, both for my wrists and ankles. “Now cuff me and put me straight on the bed, because I’m a squirmer” I said to Phil, and his (sidekick?) Freckles. “Take out the two foot paddle from my knapsack, that’s next to the briefcase, and the razor strop, and give me what I need.”

Freckles mumbled something about a safe word and I snickered at him. “I don’t need a safe word.” I said, smiling. “If you want, you can gag me, but it’s probably not necessary. I’m just going to kneel on the bed here and have you boys cuff me up, and I trust you’ll give me a nice hard time. And if I’m impressed, we’ll go to the ATM and you’ll be handsomely rewarded!”

I knelt on the bed. I’m about thirty-two, so I’m not THAT young, but I look pretty good, and Phil let one of the barely-twentysomethings put the cuffs on me.

I could tell that he had not been near a whole lot of women, as he was panting a little and being careful with the cuffs—I was kneeling on the bed with my face away from him as he locked on the cuffs on my wrists and then the others on my ankles.

“I hope these ain’t too tight, Miss” the boy said, and I turned to look at him with a rueful smile.

“Sweetie, the tighter the better. Have you ever spanked a girl before?” But of course he just blushed. My God, he was probably nineteen, and Phil and the other guys laughed.

“Leland is a little wet behin’ the ears, Gwyneth, but he’s damned willing!” Phil laughed.

“Oh go to hell, Phil” Leland mumbled, but he touched my back hesitantly.

I turned my bald head to Leland and smiled. “Leland, I’ve been a bad girl, and I need a spanking on my round little butt…can you accommodate me? Put a couple pillows under my stomach so you have a good target.”

The guys all laughed, but Phil and Freckles did the pillow work, and then they handed Leland the paddle. He was such a sweet kid, with a Mohawk and he was wearing one of those ridiculous jean jackets with the cut-off sleeves…

Leland gave my ass a half-hearted slap with the paddle. I knew he was afraid of hurting me. I turned my head to him, shaking the cue-ball at him. “C’mon, Leland, you can do better than that—you’re not a wimp, are you?”

Leland muttered something about hitting a defenseless bound woman, but then he swung the paddle harder—it was a short, thick fraternity paddle, and the second time he swung it, it connected pretty hard, and I could feel the redness gathering in my buttocks cheeks.

“Boys, if Leland isn’t up to it, it’ll have to be someone else.” I was trying to piss Leland off, I guess, and finally I think I got him. Leland began energetically swatting my buttocks, about thirty times. I didn’t make a sound, and finally, I guess his arm was tired…

Leland had a pretty good swing, but he didn’t know how to arch his back and put effort into it, scientifically, like Mother does.

Mother knows where the tender spot is just below my buttocks and my upper thighs, and is smart enough to slash the paddle on secret sensitive spots that always bring me to sure tears…but Mother is an old adversary.

Phil took up the paddle next, and thrashed me a bit, and then I suggested they take out the razor strop, and use it on my breasts…he was mystified by the chastity lock on my clitoris…I couldn’t explain that my orgasms are controlled by another, but I promised him so much pleasure with my other orifices—mouth and asshole—that he didn’t mind so much.

Of course, I was going to be so horny after serving the guys, and I couldn’t even masturbate—Sondra wouldn’t allow it—I had to wait for my chance to masturbate at the end of the month—but indeed this was a thrill!

For a time Phil and Freckles double-teamed me, one whipping my boobs with the strop while the other attended to my rear—and then Leland looked a little resentful, so I told him that I’d suck him off …and if I didn’t make him cum in three minutes he could put a cigarette out on my tender breasts.

Just after this, Phil’s “girlfriends” blondish twins improbably named Velvet and Violet showed up, and they were jealous, and took turns peeing on me…

Mother would have been so proud…

Later on in the evening, when my jaws were aching from having sucked so much cock, and I had to wipe blood and shit out of my rectum…the guys were all gone, and I’d tipped them about three hundred bucks each…I just wanted to masturbate in the motel room, and orgasm, and think about the experience.

And I couldn’t!

Because, of course I have the chastity lock on my clitoris. I can toy with it and get really, really excited, but I can’t cum. And that made me sob myself to sleep…it’s so damn frustrating. Ten times as punishing as being beaten and forced to fellate, is not being allowed to orgasm…until I see my bitch sister at the end of next month…and then MAYBE I’ll be given release. But probably not. Bitch!

August 2

“Uno!” Carmen screams, before her thorny switch hits my bare ass

“Uno” I repeat weakly, and feel the WHACK! And then “Dos”…”Tres!” By “Cinco” I am weeping softly.

When Carmen cuts a switch from the rosebush in my front yard, she always neglects to cut off the thorns, and I know she does it on purpose. “I mus’ teach ju to mind, Senora Gwyneth, to obey…to no’ make de house a peeg sty!”

But the thorns are always so clinging, they tear the sensitive skin from my tender buttocks, and I cry in misery. I just can’t take it! And Carmen has a back hand. I gave her tennis lessons for Christmas last year, tennis and racquetball, and she really can make me um, sit up and take notice, if you know what I mean?

I mean, she’s fifty-three years old, but she’s still quite gorgeous, and very, very muscular. Of course when Carmen first came to work for me, she was all respect and fear, but I had Sondra explain to her what makes Senora Gwyneth tick, and Carmen learned fast…a little too fast! And a little too well.

Carmen is my housekeeper, and when she discovers that I left papers on her clean kitchen counter, its punishment time for Gwyneth, business meeting or no business meeting.

Already this morning Carmen took my pajama bottoms down and whipped my butt cherry red for neglecting to wash toothpaste out of the sink, and then she ordered me to lick her cunt and make her huevos rancheros as an amends, but I know better than to cross the woman who makes my life orderly. At least I didn’t get an enema from her this morning!

A fortnight ago, I was giving a dinner party, and just before my guests arrived, Carmen didn’t like the tone I used with the caterers…and by George, she took me into the bedroom, ordered me to strip.

“But Carmen” I had wailed. “I have guests coming!” My old boyfriend, college pals, it was a serious and exciting party—but Carmen just gave me a cuff across my left ear and I took off my party dress fast.

And Carmen had put me in a bonnet and adult diapers, and had locked me in the bedroom, where I wailed and gnashed my teeth, and Carmen herself gave the party—she hostessed it…and I had an eight pm bedtime, except when I had to service the male and female caterers with my mouth when they came into the bedroom…and they also used my mouth to pee!

I guess Carmen told my friends that I had the flu or was out of town or something, I felt so angry and frustrated, like when Mother would let my younger siblings go out with their friends, and she’d lock me in the closet…but Carmen can be even more severe!

I was afraid that Carmen would get really angry after breakfast and let me have it on my butt with the frying pan, but she just bared her teeth at me, and I made it out the door with only the one thrashing.

Carmen teaches a lesson!

By the time I left for work this morning, I was very gingerly setting my shapely but quite sore derriere into the two-seater Miata…

When I was in the middle of our new project, I had a peculiar interruption this morning. Winslow the mail clerk came into my office, bypassing my secretary, who must’ve gone for lunch.

Normally I don’t interact with Winslow, unless I pass him in the hall. Winslow is one of those grotesque fat guys who probably live with mom, you know the type. He wears Vulcan ears to work and spends his weekends at Science Fiction conventions, running around in chain mail and that sort of thing.

Zits, mended glasses, hair that hasn’t been washed since the O.J. trial. A very lecherous type and a failure to the human race. I mean, who on earth would be a thirty-seven year old mail boy whose been there 12 years with no promotion?

“Yes, Winslow? What is it?” I asked, a bit irritated.

Winslow grinned and I saw all four of his yellow, mossy teeth.

“I saw you last week at the Thumbscrew Club, getting your butt smacked, Miz Fennelly. Ain’t the first time I saw you, either.”

My stomach churned. I try really hard to keep my private and job lives apart. It’s worked fairly well up until now. God knows, I’m a principal in this firm now and I don’t know how it might go if people knew that Ms. M.B.A. hotshot sales director was a secret, semen-sucking submissive.

I looked up at Winslow, bluffing away, and bridled. “Look Winslow, it’s none of your business what I do for fun and it was a one-time thing, a bachelorette party thing—“

“Naw, I seen you there before. I’m at the Thumbscrew every weekend, I bartend there wearing a black hood for extra money. Once your master let me put ice cubes up my ass from yer Appletini and then you ate them..

I’ve seen you peed on, whipped, made to lick up discarded cigarette butts, which saves the Club a janitor, I seen you hung by your tits, and you have nice pierced nipples, and you’ve eaten shit out of the Men’s room toilets.

I was even around for when Master Teaneck did the cool fire ant thing w here they crawled over your naked body  chewing away, and you cried and snot came out of your nose. It was hilarious, dude.”

I tried looking severely at Winslow, sort of zeroing in on one of his acne pustules expanding on his chin. I was annoyed, worried, and a little excited. Humiliation seems to do that to me, although it really shouldn’t in the workspace.

Now Winslow looked at me over my desk. “Guess what I got? I got the box of binder clips you ordered—the little black metal things, they pinch, but you got to pay me a delivery price, Gwyneth my slave girl.”

What a gross pig. I looked at him scornfully. “Winslow, I am aware you are already on probation for sexual harassment, and I think you are treading thin water here—“

But Winslow came a little closer, breathing his horrible breath and holding one of the binder clips. I knew that all I had to do was call security—hell, I’m a brown belt and could’ve put him in the hospital, but then I looked up at Winslow from my sitting position on my executive chair and then looked down at my silk blouse.

If anyone reading this journal concludes I need serious therapy, I don’t blame them. I breathed heavily and began unbuttoning my shirt, fast in case Master Winslow changed his mind. After I had my shirt unbuttoned down to my waist, and my big boobs were showing in the rose-colored demibra, I felt his filthy hand come out and yank my bra down hard.

Then he began feeling my full breasts, I guess he’d never touched anything like them before. After all, I used to model, and Winslow really is on the bottom chain of the human race.

And then came the clips. I have to admit, it wasn’t the first time I looked at the binder clips and wondered how they would feel on my nipples. I’m a sick girl. Winslow expertly fingered a nipple until it was hard, and then locked on a clip, and then did the same with the other breast.

“These’re nice titties” he mumbled, and groped a bit again, gaping with the nearsighted eyes. One of the advantages of my previous dominants even those in the biker gang I picked up recently were fairly cute…but Winslow was not an attractive specimen. Just disgusting. Sweaty, drooling…ugh.

I closed my eyes for a moment and felt Winslow twist the metal binder clip on my tender right nipple, and the pain was sharp. I moaned, and then he pulled up on the nipple and I stood, opening my eyes again. Winslow snapped his fingers and I methodically stripped off my suit, shoes, everything except my black stockings.

Winslow grabbed me by the ear and led me over to the paper cutter blade. “I should cut one of these bosoms off to keep for the guys in the mail room. What do you think, you shit-bag?”

Fully in sub space, I automatically said. “It’s your will, Master but if there’s some other way I could please you—“ So Winslow dropped to his knees and put more binder clips on my shaved clitoris and on my legs.

He toyed with my chastity lock a little bit, and I felt drool hit my stockinged foot. I would probably have to throw these  hose out—they were imported from Paris and did not take geek-drool well.

As I stood there, a knock came to the office door, and although I was panicking, Winslow was confident and in full form. He opened it slightly and then completely to let in a little curly haired twenty-something—it was a file clerk, who I’d written up for sloppiness, her name was Ramona Rewbush, and I’d actually recommend they fire her…not such a good idea.

Ramona was a cute little thing and looked at me not with surprise, but with utter contempt.

“Jesus Winslow, what did you do to Miz Fennelly?” Ramona stepped up close and twisted the binder clip on my left nipple.

“I’m just having a little fun” Winslow said, pushing his taped aviator glasses up on his pimple laden nose.

Ramona circled me, swishing her little miniskirt and then came back up front. “Hello Miz Fennelly”

“Hello, Ramona, you can call me Gwyneth if you—“

But my sentence ended in a shriek as Ramona yanked one of the binder clips off my nipple. A tear ran down my cheek, it was so painful.

“What a sissy you are. Crybaby. “ Ramona was a mean one.

I tried not to let my lip tremble.

“So what’s Miss Rich Bitch doing now? You want to write me up now?” Ramona yanked the other nipple clamp off my right breast and I burst into silent tears. Ramona slapped my jaw lightly. “You know, I didn’t get a raise this year, my third in this shitty job. This means I still got to take food stamps, you rich bitch.”

I stood there, looking ridiculous, naked except for the stockings and assorted binder clips.

As Ramona was lambasting me, Winslow had gone to the back and was methodically putting more binder clips on my full butt cheeks. My butt is so luscious, and he was worshipping it a bit, kissing it, and forgetting his master status, but…then he’d put on another damn clip!

It was so annoying. I felt like the lower classes were going all Marx-Engels on me, and I had no control.

“Gimme your belt, Winslow!” Ramona shouted, and Winslow pulled it off and handed it to her, and Ramona looped the belt in her little hand and swung it against my already bruised tits.

“This job sucks, but I got too much acne to work at the damn perfume counter at the mall, so I’m a little careless with the damn files, you all are too cheap to computerize anyway—who gives a shit…eight dollars fifty cents a damn hour.”

Ramona now swung the belt buckle and it hit me in the stomach cutting me just above my navel. I tried to grab the belt and Ramona slapped my face and kneed me in the groin, and I fell to my knees to the floor of the office.

Ramona tried to grab me by the hair and my wig came off, and my bald head made both clerical employees go into hysterics.

Then Ramona took me by the neck and shoved my face into the carpet, just like Mother used to do before she punished me. This forced my butt up, and Ramona began whipping my bare ass with the belt, knocking off the binder clips, while making me sing “100 bottles of beer on the wall.”

Finally I was covered with marks and welts and then Ramona sat on my office chair, pulled down her panties and made me munch away, while Winslow fucked me in the ass.

Then, after Ramona had cum twice, I was forced to lick my shit off Winslow’s cock and suck him to a full orgasm as well. Winslow’s brother Wendell stepped into the office, another career mail clerk, and I sucked HIM off, too.

The three of them left, laughing, and I got dressed and refreshed my makeup and went back to work. I just couldn’t believe this had happened to me…

Things were busy this morning after the Winslow debacle work, I did well on the business trip, and Mr. Godwulf was very happy. I got a call from Marcie, my secretary that Sondra called, and I was really excited. I called Sondra back and we made plans to have a late lunch. I told Marcie that I probably would not be back this afternoon, as Sondra keeps me out late…

Of course I was really hoping that Sondra had brought the key to my chastity lock and that she wanted to go back to my place, or even closer to a hotel room…but my sister is a creature of habit, and I knew deep down that Sondra, when she said I was to wait until the end of next month to get an orgasm, she probably meant it!

But we had a fun lunch (I paid, Sondra is career wise, kind of a slacker) and gossiped about friends and family. I looked at her as we were finishing chocolate mousse and said “So I guess you don’t want to take some time and go to the Hilton?”

Sondra tossed back her long red hair and grinned at me. We look so different, she wears a lot of punk rock  crap, and I of course only shop at Betsy Johnson—but we are sisters!

“Gwyneth, we can go to the Hilton, if you want, babe, but I didn’t bring your key. I told you…you pissed me off last time, and so I added three weeks to your next orgasm cycle and three weeks is just that. But if you want to lick me a little between my legs, we can do the Hilton, it’s not like I have anything else to do!”

I bit back tears. She is such a bitch! Of course I can give her an orgasm, but I don’t get one. I’ll end up giving her thirty orgasms, and wear my mouth out doing it, I’m still tired from servicing Carmen this morning, but Sondra can’t let me out of my lock just for a quick masturbation session.

She’s mad because the last time I came, I was rubbing my clit against her boot, and Sondra said I could cum in no more or less than three minutes on the dot, and of course I came too soon. Better than going over, because then she would’ve pulled her boot away, and I would’ve had to wait another two weeks before the lock came off again!

But God, how vengeful to give me  a two month chastity sentence—and she’d also used her piece of cut off garden hose, which always leaves me covered in black and blue welts…but I’m a woman, dammit…I want to cum!

Of course if I said that, Sondra would just tell me to pick up my key at her place and go get laid, if I want. But I want to serve Sondra, I love Sondra…I’m excited being kept on the edge, but TWO MONTHS. Jesus.

We ended up going to the Hilton (I paid, again) and we went upstairs and Sondra took off her leather jacket and leaned against the wall in her little Black Sabbath T-shirt while I stripped and knelt in front of her,  dropping my wig on the floor.

Carmen checked this morning after I shaved my head, and plucked out (painfully) a few hairs I missed, as well as plucking a few from my vagina…Carmen is quite into penalizing me for not doing a thorough enough job. She threatens to come to work, or to see me on the street and yank off my wig so all can “see ju as a leel baby, a whiny baby, Senora Gwyneth.”.

But my sister looked disdainfully at my bowed cue-ball head and then she took one of her high heels off and whacked me right in the middle of my head, with the spike, and it bled a little and I had to hold back the tears.

A moment later, Sondra had me across her lap, and had Mother’s elephant-tusk hairbrush, and it was turning my rump into roast…big time… and then she shoved me between her legs, and I dove that muff like no one’s business…

The bitch, my younger sister, the fuck-up who was expelled from school while I was on the honor roll…she cuffed my hands behind my back, and DID produce the key to my chastity lock!

And she released me…oh yes, and she diddled my little clit until I was on the verge of cumming, and then took me to the bathtub and diddled me some more until I became closer and closer to cumming and I was thanking Sondra for this incredible gift, calling the little bitch “Mistress” and “Goddess” because I was so damn GRATEFUL…

And then, just as I was about to cum, she turned on the cold shower—ice cold, and I was cuffed, wrists and ankles, and I lay there wriggling and screaming, not only was I not able to cum, but I was afraid I’d get freaking pneumonia, the water was so cold…and she left me there for three hours while she got drunk in the bar downstairs…

I hate Sondra…and I love her!

When Sondra came back up, it was with a drunk she met in the bar. I was screaming in pain from the ice cold water, but Sondra dragged me out by my ear, and uncuffed me.

The drunken computer sales dude, or whatever he was, just gaped as Sondra ordered me to get on my hands and knees (and she locked the chastity lock back on my clit, the bitch) and then she announced “Gilbert says he (hic) can play better chess than I can, so we’re going to balance (hic) the board on your back and play chess, and you better not move, Sis….or I’ll put you back in the bathtub, or even lock you under the sink like I used to do when we were (hic) kids.”

I’ve been trained to be motionless on hands and knees before while my parents or siblings used my back for a table (how did I get to be the scapegoat? Who knows) and so I knew what to do while these two drunks sat on each side of me on little stools, but of course Gilbert was all horny to stick his dick in my mouth, and Sondra said that if he beat her in chess, I’d give him a super blowjob, and if not, he’d have to give her fifty bucks…

And I was motionless, but then one of the pawns fell on the floor, and Sondra got really pissed off! She took her rubber hose piece out of her purse and bent me over the hotel bed

(I was protesting vociferously that I had not moved an inch) and she gave me fifty, and turned my entire back, buttocks and upper thighs purple, while Gil watched and pounded his pud as it stuck out of his zipper. And then I sucked him off…and then he wanted to use the hose on me, but on my nice big boobs…and guess who let him?

Later on, they sneaked me downstairs to the basement of the Hilton, and Sondra took a chain and looped it through the piercings in my nipples, and also looped the chain around a pole holding the ceiling up, so that the pole was in between the chain and me, or in other words I couldn’t pull away from the pole without ripping my nipples off. Then Sondra cuffed my hands behind my back and left me there, kneeling and naked in the basement, and didn’t come back to get me until three o’clock the next morning.

I type this with sore nipples and ohhh…what a headache. Kneeling in a cold hotel basement, with more than a few rats running around, and having my back cramped, because I couldn’t move away from the pole was just horrible.

As I said, I love Sondra, and I hate her…but she is certainly imaginative, isn’t she?

Also, I got a voicemail when I got home from my friend Gervaise, she was once a sub of MINE, and is very much a slave girl. I got Gervaise in touch with Leland, the young gang biker and they are very much involved, and she is serving Leland with vigor.

Leland is very impressed that Gervaise can hold her hand out and have cigarettes burned on it without complaining. I, of course can have them put out in my mouth, but not to be competitive. Leland and Gervaise may be some kinda couple now.

I wonder how long it will take for Leland to discover that Gervaise is not a woman born woman?

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